Merge public-gh/master into feature/plugin-runtime-instance-cleanup

cli/src/__tests__/agent-jwt-env.test.ts

@@ -4,7 +4,9 @@ import path from "node:path";
 import { afterEach, beforeEach, describe, expect, it } from "vitest";
 import {
   ensureAgentJwtSecret,
+  mergePaperclipEnvEntries,
   readAgentJwtSecretFromEnv,
+  readPaperclipEnvEntries,
   resolveAgentJwtEnvFile,
 } from "../config/env.js";
 import { agentJwtSecretCheck } from "../checks/agent-jwt-secret-check.js";
@@ -58,4 +60,20 @@ describe("agent jwt env helpers", () => {
     const result = agentJwtSecretCheck(configPath);
     expect(result.status).toBe("pass");
   });
+
+  it("quotes hash-prefixed env values so dotenv round-trips them", () => {
+    const configPath = tempConfigPath();
+    const envPath = resolveAgentJwtEnvFile(configPath);
+
+    mergePaperclipEnvEntries(
+      {
+        PAPERCLIP_WORKTREE_COLOR: "#439edb",
+      },
+      envPath,
+    );
+
+    const contents = fs.readFileSync(envPath, "utf-8");
+    expect(contents).toContain('PAPERCLIP_WORKTREE_COLOR="#439edb"');
+    expect(readPaperclipEnvEntries(envPath).PAPERCLIP_WORKTREE_COLOR).toBe("#439edb");
+  });
 });

cli/src/__tests__/worktree.test.ts

@@ -7,6 +7,7 @@ import {
   copyGitHooksToWorktreeGitDir,
   copySeededSecretsKey,
   rebindWorkspaceCwd,
+  resolveSourceConfigPath,
   resolveGitWorktreeAddArgs,
   resolveWorktreeMakeTargetPath,
   worktreeInitCommand,
@@ -293,7 +294,7 @@ describe("worktree helpers", () => {
       const envContents = fs.readFileSync(envPath, "utf8");
       expect(envContents).toContain("PAPERCLIP_AGENT_JWT_SECRET=worktree-shared-secret");
       expect(envContents).toContain("PAPERCLIP_WORKTREE_NAME=repo");
-      expect(envContents).toMatch(/PAPERCLIP_WORKTREE_COLOR=#[0-9a-f]{6}/);
+      expect(envContents).toMatch(/PAPERCLIP_WORKTREE_COLOR=\"#[0-9a-f]{6}\"/);
     } finally {
       process.chdir(originalCwd);
       if (originalJwtSecret === undefined) {
@@ -305,6 +306,59 @@ describe("worktree helpers", () => {
     }
   });
 
+  it("defaults the seed source config to the current repo-local Paperclip config", () => {
+    const tempRoot = fs.mkdtempSync(path.join(os.tmpdir(), "paperclip-worktree-source-config-"));
+    const repoRoot = path.join(tempRoot, "repo");
+    const localConfigPath = path.join(repoRoot, ".paperclip", "config.json");
+    const originalCwd = process.cwd();
+    const originalPaperclipConfig = process.env.PAPERCLIP_CONFIG;
+
+    try {
+      fs.mkdirSync(path.dirname(localConfigPath), { recursive: true });
+      fs.writeFileSync(localConfigPath, JSON.stringify(buildSourceConfig()), "utf8");
+      delete process.env.PAPERCLIP_CONFIG;
+      process.chdir(repoRoot);
+
+      expect(fs.realpathSync(resolveSourceConfigPath({}))).toBe(fs.realpathSync(localConfigPath));
+    } finally {
+      process.chdir(originalCwd);
+      if (originalPaperclipConfig === undefined) {
+        delete process.env.PAPERCLIP_CONFIG;
+      } else {
+        process.env.PAPERCLIP_CONFIG = originalPaperclipConfig;
+      }
+      fs.rmSync(tempRoot, { recursive: true, force: true });
+    }
+  });
+
+  it("preserves the source config path across worktree:make cwd changes", () => {
+    const tempRoot = fs.mkdtempSync(path.join(os.tmpdir(), "paperclip-worktree-source-override-"));
+    const sourceConfigPath = path.join(tempRoot, "source", "config.json");
+    const targetRoot = path.join(tempRoot, "target");
+    const originalCwd = process.cwd();
+    const originalPaperclipConfig = process.env.PAPERCLIP_CONFIG;
+
+    try {
+      fs.mkdirSync(path.dirname(sourceConfigPath), { recursive: true });
+      fs.mkdirSync(targetRoot, { recursive: true });
+      fs.writeFileSync(sourceConfigPath, JSON.stringify(buildSourceConfig()), "utf8");
+      delete process.env.PAPERCLIP_CONFIG;
+      process.chdir(targetRoot);
+
+      expect(resolveSourceConfigPath({ sourceConfigPathOverride: sourceConfigPath })).toBe(
+        path.resolve(sourceConfigPath),
+      );
+    } finally {
+      process.chdir(originalCwd);
+      if (originalPaperclipConfig === undefined) {
+        delete process.env.PAPERCLIP_CONFIG;
+      } else {
+        process.env.PAPERCLIP_CONFIG = originalPaperclipConfig;
+      }
+      fs.rmSync(tempRoot, { recursive: true, force: true });
+    }
+  });
+
   it("rebinds same-repo workspace paths onto the current worktree root", () => {
     expect(
       rebindWorkspaceCwd({

cli/src/commands/worktree.ts

@@ -56,6 +56,7 @@ type WorktreeInitOptions = {
   fromConfig?: string;
   fromDataDir?: string;
   fromInstance?: string;
+  sourceConfigPathOverride?: string;
   serverPort?: number;
   dbPort?: number;
   seed?: boolean;
@@ -426,8 +427,12 @@ async function rebindSeededProjectWorkspaces(input: {
   }
 }
 
-function resolveSourceConfigPath(opts: WorktreeInitOptions): string {
+export function resolveSourceConfigPath(opts: WorktreeInitOptions): string {
+  if (opts.sourceConfigPathOverride) return path.resolve(opts.sourceConfigPathOverride);
   if (opts.fromConfig) return path.resolve(opts.fromConfig);
+  if (!opts.fromDataDir && !opts.fromInstance) {
+    return resolveConfigPath();
+  }
   const sourceHome = path.resolve(expandHomePrefix(opts.fromDataDir ?? "~/.paperclip"));
   const sourceInstanceId = sanitizeWorktreeInstanceId(opts.fromInstance ?? "default");
   return path.resolve(sourceHome, "instances", sourceInstanceId, "config.json");
@@ -751,6 +756,7 @@ export async function worktreeMakeCommand(nameArg: string, opts: WorktreeMakeOpt
   const name = resolveWorktreeMakeName(nameArg);
   const startPoint = resolveWorktreeStartPoint(opts.startPoint);
   const sourceCwd = process.cwd();
+  const sourceConfigPath = resolveSourceConfigPath(opts);
   const targetPath = resolveWorktreeMakeTargetPath(name);
   if (existsSync(targetPath)) {
     throw new Error(`Target path already exists: ${targetPath}`);
@@ -810,6 +816,7 @@ export async function worktreeMakeCommand(nameArg: string, opts: WorktreeMakeOpt
     await runWorktreeInit({
       ...opts,
       name,
+      sourceConfigPathOverride: sourceConfigPath,
     });
   } catch (error) {
     throw error;

cli/src/config/env.ts

@@ -22,11 +22,18 @@ function parseEnvFile(contents: string) {
   }
 }
 
+function formatEnvValue(value: string): string {
+  if (/^[A-Za-z0-9_./:@-]+$/.test(value)) {
+    return value;
+  }
+  return JSON.stringify(value);
+}
+
 function renderEnvFile(entries: Record<string, string>) {
   const lines = [
     "# Paperclip environment variables",
     "# Generated by Paperclip CLI commands",
-    ...Object.entries(entries).map(([key, value]) => `${key}=${value}`),
+    ...Object.entries(entries).map(([key, value]) => `${key}=${formatEnvValue(value)}`),
     "",
   ];
   return lines.join("\n");

doc/DEVELOPING.md

@@ -142,7 +142,7 @@ This command:
 - creates an isolated instance under `~/.paperclip-worktrees/instances/<worktree-id>/`
 - when run inside a linked git worktree, mirrors the effective git hooks into that worktree's private git dir
 - picks a free app port and embedded PostgreSQL port
-- by default seeds the isolated DB in `minimal` mode from your main instance via a logical SQL snapshot
+- by default seeds the isolated DB in `minimal` mode from the current effective Paperclip instance/config (repo-local worktree config when present, otherwise the default instance) via a logical SQL snapshot
 
 Seed modes:
 

doc/SPEC-implementation.md

@@ -330,6 +330,34 @@ Operational policy:
   - `asset_id` uuid fk not null
   - `issue_comment_id` uuid fk null
 
+## 7.15 `documents` + `document_revisions` + `issue_documents`
+
+- `documents` stores editable text-first documents:
+  - `id` uuid pk
+  - `company_id` uuid fk not null
+  - `title` text null
+  - `format` text not null (`markdown`)
+  - `latest_body` text not null
+  - `latest_revision_id` uuid null
+  - `latest_revision_number` int not null
+  - `created_by_agent_id` uuid fk null
+  - `created_by_user_id` uuid/text fk null
+  - `updated_by_agent_id` uuid fk null
+  - `updated_by_user_id` uuid/text fk null
+- `document_revisions` stores append-only history:
+  - `id` uuid pk
+  - `company_id` uuid fk not null
+  - `document_id` uuid fk not null
+  - `revision_number` int not null
+  - `body` text not null
+  - `change_summary` text null
+- `issue_documents` links documents to issues with a stable workflow key:
+  - `id` uuid pk
+  - `company_id` uuid fk not null
+  - `issue_id` uuid fk not null
+  - `document_id` uuid fk not null
+  - `key` text not null (`plan`, `design`, `notes`, etc.)
+
 ## 8. State Machines
 
 ## 8.1 Agent Status
@@ -441,6 +469,11 @@ All endpoints are under `/api` and return JSON.
 - `POST /companies/:companyId/issues`
 - `GET /issues/:issueId`
 - `PATCH /issues/:issueId`
+- `GET /issues/:issueId/documents`
+- `GET /issues/:issueId/documents/:key`
+- `PUT /issues/:issueId/documents/:key`
+- `GET /issues/:issueId/documents/:key/revisions`
+- `DELETE /issues/:issueId/documents/:key`
 - `POST /issues/:issueId/checkout`
 - `POST /issues/:issueId/release`
 - `POST /issues/:issueId/comments`

doc/plans/2026-03-13-TOKEN-OPTIMIZATION-PLAN.md

@@ -118,10 +118,18 @@ Result:
 
 Local adapters inject repo skills into runtime skill directories.
 
+Important `codex_local` nuance:
+
+- Codex does not read skills directly from the active worktree.
+- Paperclip discovers repo skills from the current checkout, then symlinks them into `$CODEX_HOME/skills` or `~/.codex/skills`.
+- If an existing Paperclip skill symlink already points at another live checkout, the current implementation skips it instead of repointing it.
+- This can leave Codex using stale skill content from a different worktree even after Paperclip-side skill changes land.
+- That is both a correctness risk and a token-analysis risk, because runtime behavior may not reflect the instructions in the checkout being tested.
+
 Current repo skill sizes:
 
 - `skills/paperclip/SKILL.md`: 17,441 bytes
-- `skills/create-agent-adapter/SKILL.md`: 31,832 bytes
+- `.agents/skills/create-agent-adapter/SKILL.md`: 31,832 bytes
 - `skills/paperclip-create-agent/SKILL.md`: 4,718 bytes
 - `skills/para-memory-files/SKILL.md`: 3,978 bytes
 
@@ -215,6 +223,8 @@ This is the right version of the discussion’s bootstrap idea.
 
 Static instructions and dynamic wake context have different cache behavior and should be modeled separately.
 
+For `codex_local`, this also requires isolating the Codex skill home per worktree or teaching Paperclip to repoint its own skill symlinks when the source checkout changes. Otherwise prompt and skill improvements in the active worktree may not reach the running agent.
+
 ### Success criteria
 
 - fresh-session prompts can remain richer without inflating every resumed heartbeat
@@ -305,6 +315,9 @@ Even when reuse is desirable, some sessions become too expensive to keep alive i
   - `para-memory-files`
   - `create-agent-adapter`
 - Expose active skill set in agent config and run metadata.
+- For `codex_local`, either:
+  - run with a worktree-specific `CODEX_HOME`, or
+  - treat Paperclip-owned Codex skill symlinks as repairable when they point at a different checkout
 
 ### Why
 
@@ -363,6 +376,7 @@ Initial targets:
 6. Rewrite `skills/paperclip/SKILL.md` around delta-fetch behavior.
 7. Add session rotation with carry-forward summaries.
 8. Replace global skill injection with explicit allowlists.
+9. Fix `codex_local` skill resolution so worktree-local skill changes reliably reach the runtime.
 
 ## Recommendation
 

doc/plans/2026-03-13-agent-evals-framework.md

@@ -0,0 +1,775 @@
+# Agent Evals Framework Plan
+
+Date: 2026-03-13
+
+## Context
+
+We need evals for the thing Paperclip actually ships:
+
+- agent behavior produced by adapter config
+- prompt templates and bootstrap prompts
+- skill sets and skill instructions
+- model choice
+- runtime policy choices that affect outcomes and cost
+
+We do **not** primarily need a fine-tuning pipeline.
+We need a regression framework that can answer:
+
+- if we change prompts or skills, do agents still do the right thing?
+- if we switch models, what got better, worse, or more expensive?
+- if we optimize tokens, did we preserve task outcomes?
+- can we grow the suite over time from real Paperclip usage?
+
+This plan is based on:
+
+- `doc/GOAL.md`
+- `doc/PRODUCT.md`
+- `doc/SPEC-implementation.md`
+- `docs/agents-runtime.md`
+- `doc/plans/2026-03-13-TOKEN-OPTIMIZATION-PLAN.md`
+- Discussion #449: <https://github.com/paperclipai/paperclip/discussions/449>
+- OpenAI eval best practices: <https://developers.openai.com/api/docs/guides/evaluation-best-practices>
+- Promptfoo docs: <https://www.promptfoo.dev/docs/configuration/test-cases/> and <https://www.promptfoo.dev/docs/providers/custom-api/>
+- LangSmith complex agent eval docs: <https://docs.langchain.com/langsmith/evaluate-complex-agent>
+- Braintrust dataset/scorer docs: <https://www.braintrust.dev/docs/annotate/datasets> and <https://www.braintrust.dev/docs/evaluate/write-scorers>
+
+## Recommendation
+
+Paperclip should take a **two-stage approach**:
+
+1. **Start with Promptfoo now** for narrow, prompt-and-skill behavior evals across models.
+2. **Grow toward a first-party, repo-local eval harness in TypeScript** for full Paperclip scenario evals.
+
+So the recommendation is no longer “skip Promptfoo.” It is:
+
+- use Promptfoo as the fastest bootstrap layer
+- keep eval cases and fixtures in this repo
+- avoid making Promptfoo config the deepest long-term abstraction
+
+More specifically:
+
+1. The canonical eval definitions should live in this repo under a top-level `evals/` directory.
+2. `v0` should use Promptfoo to run focused test cases across models and providers.
+3. The longer-term harness should run **real Paperclip scenarios** against seeded companies/issues/agents, not just raw prompt completions.
+4. The scoring model should combine:
+   - deterministic checks
+   - structured rubric scoring
+   - pairwise candidate-vs-baseline judging
+   - efficiency metrics from normalized usage/cost telemetry
+5. The framework should compare **bundles**, not just models.
+
+A bundle is:
+
+- adapter type
+- model id
+- prompt template(s)
+- bootstrap prompt template
+- skill allowlist / skill content version
+- relevant runtime flags
+
+That is the right unit because that is what actually changes behavior in Paperclip.
+
+## Why This Is The Right Shape
+
+### 1. We need to evaluate system behavior, not only prompt output
+
+Prompt-only tools are useful, but Paperclip’s real failure modes are often:
+
+- wrong issue chosen
+- wrong API call sequence
+- bad delegation
+- failure to respect approval boundaries
+- stale session behavior
+- over-reading context
+- claiming completion without producing artifacts or comments
+
+Those are control-plane behaviors. They require scenario setup, execution, and trace inspection.
+
+### 2. The repo is already TypeScript-first
+
+The existing monorepo already uses:
+
+- `pnpm`
+- `tsx`
+- `vitest`
+- TypeScript across server, UI, shared contracts, and adapters
+
+A TypeScript-first harness will fit the repo and CI better than introducing a Python-first test subsystem as the default path.
+
+Python can stay optional later for specialty scorers or research experiments.
+
+### 3. We need provider/model comparison without vendor lock-in
+
+OpenAI’s guidance is directionally right:
+
+- eval early and often
+- use task-specific evals
+- log everything
+- prefer pairwise/comparison-style judging over open-ended scoring
+
+But OpenAI’s Evals API is not the right control plane for Paperclip as the primary system because our target is explicitly multi-model and multi-provider.
+
+### 4. Hosted eval products are useful, and Promptfoo is the right bootstrap tool
+
+The current tradeoff:
+
+- Promptfoo is very good for local, repo-based prompt/provider matrices and CI integration.
+- LangSmith is strong on trajectory-style agent evals.
+- Braintrust has a clean dataset + scorer + experiment model and strong TypeScript support.
+
+The community suggestion is directionally right:
+
+- Promptfoo lets us start small
+- it supports simple assertions like contains / not-contains / regex / custom JS
+- it can run the same cases across multiple models
+- it supports OpenRouter
+- it can move into CI later
+
+That makes it the best `v0` tool for “did this prompt/skill/model change obviously regress?”
+
+But Paperclip should still avoid making a hosted platform or a third-party config format the core abstraction before we have our own stable eval model.
+
+The right move is:
+
+- start with Promptfoo for quick wins
+- keep the data portable and repo-owned
+- build a thin first-party harness around Paperclip concepts as the system grows
+- optionally export to or integrate with other tools later if useful
+
+## What We Should Evaluate
+
+We should split evals into four layers.
+
+### Layer 1: Deterministic contract evals
+
+These should require no judge model.
+
+Examples:
+
+- agent comments on the assigned issue
+- no mutation outside the agent’s company
+- approval-required actions do not bypass approval flow
+- task transitions are legal
+- output contains required structured fields
+- artifact links exist when the task required an artifact
+- no full-thread refetch on delta-only cases once the API supports it
+
+These are cheap, reliable, and should be the first line of defense.
+
+### Layer 2: Single-step behavior evals
+
+These test narrow behaviors in isolation.
+
+Examples:
+
+- chooses the correct issue from inbox
+- writes a reasonable first status comment
+- decides to ask for approval instead of acting directly
+- delegates to the correct report
+- recognizes blocked state and reports it clearly
+
+These are the closest thing to prompt evals, but still framed in Paperclip terms.
+
+### Layer 3: End-to-end scenario evals
+
+These run a full heartbeat or short sequence of heartbeats against a seeded scenario.
+
+Examples:
+
+- new assignment pickup
+- long-thread continuation
+- mention-triggered clarification
+- approval-gated hire request
+- manager escalation
+- workspace coding task that must leave a meaningful issue update
+
+These should evaluate both final state and trace quality.
+
+### Layer 4: Efficiency and regression evals
+
+These are not “did the answer look good?” evals. They are “did we preserve quality while improving cost/latency?” evals.
+
+Examples:
+
+- normalized input tokens per successful heartbeat
+- normalized tokens per completed issue
+- session reuse rate
+- full-thread reload rate
+- wall-clock duration
+- cost per successful scenario
+
+This layer is especially important for token optimization work.
+
+## Core Design
+
+## 1. Canonical object: `EvalCase`
+
+Each eval case should define:
+
+- scenario setup
+- target bundle(s)
+- execution mode
+- expected invariants
+- scoring rubric
+- tags/metadata
+
+Suggested shape:
+
+```ts
+type EvalCase = {
+  id: string;
+  description: string;
+  tags: string[];
+  setup: {
+    fixture: string;
+    agentId: string;
+    trigger: "assignment" | "timer" | "on_demand" | "comment" | "approval";
+  };
+  inputs?: Record<string, unknown>;
+  checks: {
+    hard: HardCheck[];
+    rubric?: RubricCheck[];
+    pairwise?: PairwiseCheck[];
+  };
+  metrics: MetricSpec[];
+};
+```
+
+The important part is that the case is about a Paperclip scenario, not a standalone prompt string.
+
+## 2. Canonical object: `EvalBundle`
+
+Suggested shape:
+
+```ts
+type EvalBundle = {
+  id: string;
+  adapter: string;
+  model: string;
+  promptTemplate: string;
+  bootstrapPromptTemplate?: string;
+  skills: string[];
+  flags?: Record<string, string | number | boolean>;
+};
+```
+
+Every comparison run should say which bundle was tested.
+
+This avoids the common mistake of saying “model X is better” when the real change was model + prompt + skills + runtime behavior.
+
+## 3. Canonical output: `EvalTrace`
+
+We should capture a normalized trace for scoring:
+
+- run ids
+- prompts actually sent
+- session reuse metadata
+- issue mutations
+- comments created
+- approvals requested
+- artifacts created
+- token/cost telemetry
+- timing
+- raw outputs
+
+The scorer layer should never need to scrape ad hoc logs.
+
+## Scoring Framework
+
+## 1. Hard checks first
+
+Every eval should start with pass/fail checks that can invalidate the run immediately.
+
+Examples:
+
+- touched wrong company
+- skipped required approval
+- no issue update produced
+- returned malformed structured output
+- marked task done without required artifact
+
+If a hard check fails, the scenario fails regardless of style or judge score.
+
+## 2. Rubric scoring second
+
+Rubric scoring should use narrow criteria, not vague “how good was this?” prompts.
+
+Good rubric dimensions:
+
+- task understanding
+- governance compliance
+- useful progress communication
+- correct delegation
+- evidence of completion
+- concision / unnecessary verbosity
+
+Each rubric should be a small 0-1 or 0-2 decision, not a mushy 1-10 scale.
+
+## 3. Pairwise judging for candidate vs baseline
+
+OpenAI’s eval guidance is right that LLMs are better at discrimination than open-ended generation.
+
+So for non-deterministic quality checks, the default pattern should be:
+
+- run baseline bundle on the case
+- run candidate bundle on the same case
+- ask a judge model which is better on explicit criteria
+- allow `baseline`, `candidate`, or `tie`
+
+This is better than asking a judge for an absolute quality score with no anchor.
+
+## 4. Efficiency scoring is separate
+
+Do not bury efficiency inside a single blended quality score.
+
+Record it separately:
+
+- quality score
+- cost score
+- latency score
+
+Then compute a summary decision such as:
+
+- candidate is acceptable only if quality is non-inferior and efficiency is improved
+
+That is much easier to reason about than one magic number.
+
+## Suggested Decision Rule
+
+For PR gating:
+
+1. No hard-check regressions.
+2. No significant regression on required scenario pass rate.
+3. No significant regression on key rubric dimensions.
+4. If the change is token-optimization-oriented, require efficiency improvement on target scenarios.
+
+For deeper comparison reports, show:
+
+- pass rate
+- pairwise wins/losses/ties
+- median normalized tokens
+- median wall-clock time
+- cost deltas
+
+## Dataset Strategy
+
+We should explicitly build the dataset from three sources.
+
+### 1. Hand-authored seed cases
+
+Start here.
+
+These should cover core product invariants:
+
+- assignment pickup
+- status update
+- blocked reporting
+- delegation
+- approval request
+- cross-company access denial
+- issue comment follow-up
+
+These are small, clear, and stable.
+
+### 2. Production-derived cases
+
+Per OpenAI’s guidance, we should log everything and mine real usage for eval cases.
+
+Paperclip should grow eval coverage by promoting real runs into cases when we see:
+
+- regressions
+- interesting failures
+- edge cases
+- high-value success patterns worth preserving
+
+The initial version can be manual:
+
+- take a real run
+- redact/normalize it
+- convert it into an `EvalCase`
+
+Later we can automate trace-to-case generation.
+
+### 3. Adversarial and guardrail cases
+
+These should intentionally probe failure modes:
+
+- approval bypass attempts
+- wrong-company references
+- stale context traps
+- irrelevant long threads
+- misleading instructions in comments
+- verbosity traps
+
+This is where promptfoo-style red-team ideas can become useful later, but it is not the first slice.
+
+## Repo Layout
+
+Recommended initial layout:
+
+```text
+evals/
+  README.md
+  promptfoo/
+    promptfooconfig.yaml
+    prompts/
+    cases/
+  cases/
+    core/
+    approvals/
+    delegation/
+    efficiency/
+  fixtures/
+    companies/
+    issues/
+  bundles/
+    baseline/
+    experiments/
+  runners/
+    scenario-runner.ts
+    compare-runner.ts
+  scorers/
+    hard/
+    rubric/
+    pairwise/
+  judges/
+    rubric-judge.ts
+    pairwise-judge.ts
+  lib/
+    types.ts
+    traces.ts
+    metrics.ts
+  reports/
+    .gitignore
+```
+
+Why top-level `evals/`:
+
+- it makes evals feel first-class
+- it avoids hiding them inside `server/` even though they span adapters and runtime behavior
+- it leaves room for both TS and optional Python helpers later
+- it gives us a clean place for Promptfoo `v0` config plus the later first-party runner
+
+## Execution Model
+
+The harness should support three modes.
+
+### Mode A: Cheap local smoke
+
+Purpose:
+
+- run on PRs
+- keep cost low
+- catch obvious regressions
+
+Characteristics:
+
+- 5 to 20 cases
+- 1 or 2 bundles
+- mostly hard checks and narrow rubrics
+
+### Mode B: Candidate vs baseline compare
+
+Purpose:
+
+- evaluate a prompt/skill/model change before merge
+
+Characteristics:
+
+- paired runs
+- pairwise judging enabled
+- quality + efficiency diff report
+
+### Mode C: Nightly broader matrix
+
+Purpose:
+
+- compare multiple models and bundles
+- grow historical benchmark data
+
+Characteristics:
+
+- larger case set
+- multiple models
+- more expensive rubric/pairwise judging
+
+## CI and Developer Workflow
+
+Suggested commands:
+
+```sh
+pnpm evals:smoke
+pnpm evals:compare --baseline baseline/codex-default --candidate experiments/codex-lean-skillset
+pnpm evals:nightly
+```
+
+PR behavior:
+
+- run `evals:smoke` on prompt/skill/adapter/runtime changes
+- optionally trigger `evals:compare` for labeled PRs or manual runs
+
+Nightly behavior:
+
+- run larger matrix
+- save report artifact
+- surface trend lines on pass rate, pairwise wins, and efficiency
+
+## Framework Comparison
+
+## Promptfoo
+
+Best use for Paperclip:
+
+- prompt-level micro-evals
+- provider/model comparison
+- quick local CI integration
+- custom JS assertions and custom providers
+- bootstrap-layer evals for one skill or one agent workflow
+
+What changed in this recommendation:
+
+- Promptfoo is now the recommended **starting point**
+- especially for “one skill, a handful of cases, compare across models”
+
+Why it still should not be the only long-term system:
+
+- its primary abstraction is still prompt/provider/test-case oriented
+- Paperclip needs scenario setup, control-plane state inspection, and multi-step traces as first-class concepts
+
+Recommendation:
+
+- use Promptfoo first
+- store Promptfoo config and cases in-repo under `evals/promptfoo/`
+- use custom JS/TS assertions and, if needed later, a custom provider that calls Paperclip scenario runners
+- do not make Promptfoo YAML the only canonical Paperclip eval format once we outgrow prompt-level evals
+
+## LangSmith
+
+What it gets right:
+
+- final response evals
+- trajectory evals
+- single-step evals
+
+Why not the primary system today:
+
+- stronger fit for teams already centered on LangChain/LangGraph
+- introduces hosted/external workflow gravity before our own eval model is stable
+
+Recommendation:
+
+- copy the trajectory/final/single-step taxonomy
+- do not adopt the platform as the default requirement
+
+## Braintrust
+
+What it gets right:
+
+- TypeScript support
+- clean dataset/task/scorer model
+- production logging to datasets
+- experiment comparison over time
+
+Why not the primary system today:
+
+- still externalizes the canonical dataset and review workflow
+- we are not yet at the maturity where hosted experiment management should define the shape of the system
+
+Recommendation:
+
+- borrow its dataset/scorer/experiment mental model
+- revisit once we want hosted review and experiment history at scale
+
+## OpenAI Evals / Evals API
+
+What it gets right:
+
+- strong eval principles
+- emphasis on task-specific evals
+- continuous evaluation mindset
+
+Why not the primary system:
+
+- Paperclip must compare across models/providers
+- we do not want our primary eval runner coupled to one model vendor
+
+Recommendation:
+
+- use the guidance
+- do not use it as the core Paperclip eval runtime
+
+## First Implementation Slice
+
+The first version should be intentionally small.
+
+## Phase 0: Promptfoo bootstrap
+
+Build:
+
+- `evals/promptfoo/promptfooconfig.yaml`
+- 5 to 10 focused cases for one skill or one agent workflow
+- model matrix using the providers we care about most
+- mostly deterministic assertions:
+  - contains
+  - not-contains
+  - regex
+  - custom JS assertions
+
+Target scope:
+
+- one skill, or one narrow workflow such as assignment pickup / first status update
+- compare a small set of bundles across several models
+
+Success criteria:
+
+- we can run one command and compare outputs across models
+- prompt/skill regressions become visible quickly
+- the team gets signal before building heavier infrastructure
+
+## Phase 1: Skeleton and core cases
+
+Build:
+
+- `evals/` scaffold
+- `EvalCase`, `EvalBundle`, `EvalTrace` types
+- scenario runner for seeded local cases
+- 10 hand-authored core cases
+- hard checks only
+
+Target cases:
+
+- assigned issue pickup
+- write progress comment
+- ask for approval when required
+- respect company boundary
+- report blocked state
+- avoid marking done without artifact/comment evidence
+
+Success criteria:
+
+- a developer can run a local smoke suite
+- prompt/skill changes can fail the suite deterministically
+- Promptfoo `v0` cases either migrate into or coexist with this layer cleanly
+
+## Phase 2: Pairwise and rubric layer
+
+Build:
+
+- rubric scorer interface
+- pairwise judge runner
+- candidate vs baseline compare command
+- markdown/html report output
+
+Success criteria:
+
+- model/prompt bundle changes produce a readable diff report
+- we can tell “better”, “worse”, or “same” on curated scenarios
+
+## Phase 3: Efficiency integration
+
+Build:
+
+- normalized token/cost metrics into eval traces
+- cost and latency comparisons
+- efficiency gates for token optimization work
+
+Dependency:
+
+- this should align with the telemetry normalization work in `2026-03-13-TOKEN-OPTIMIZATION-PLAN.md`
+
+Success criteria:
+
+- quality and efficiency can be judged together
+- token-reduction work no longer relies on anecdotal improvements
+
+## Phase 4: Production-case ingestion
+
+Build:
+
+- tooling to promote real runs into new eval cases
+- metadata tagging
+- failure corpus growth process
+
+Success criteria:
+
+- the eval suite grows from real product behavior instead of staying synthetic
+
+## Initial Case Categories
+
+We should start with these categories:
+
+1. `core.assignment_pickup`
+2. `core.progress_update`
+3. `core.blocked_reporting`
+4. `governance.approval_required`
+5. `governance.company_boundary`
+6. `delegation.correct_report`
+7. `threads.long_context_followup`
+8. `efficiency.no_unnecessary_reloads`
+
+That is enough to start catching the classes of regressions we actually care about.
+
+## Important Guardrails
+
+### 1. Do not rely on judge models alone
+
+Every important scenario needs deterministic checks first.
+
+### 2. Do not gate PRs on a single noisy score
+
+Use pass/fail invariants plus a small number of stable rubric or pairwise checks.
+
+### 3. Do not confuse benchmark score with product quality
+
+The suite must keep growing from real runs, otherwise it will become a toy benchmark.
+
+### 4. Do not evaluate only final output
+
+Trajectory matters for agents:
+
+- did they call the right Paperclip APIs?
+- did they ask for approval?
+- did they communicate progress?
+- did they choose the right issue?
+
+### 5. Do not make the framework vendor-shaped
+
+Our eval model should survive changes in:
+
+- judge provider
+- candidate provider
+- adapter implementation
+- hosted tooling choices
+
+## Open Questions
+
+1. Should the first scenario runner invoke the real server over HTTP, or call services directly in-process?
+   My recommendation: start in-process for speed, then add HTTP-mode coverage once the model stabilizes.
+
+2. Should we support Python scorers in v1?
+   My recommendation: no. Keep v1 all-TypeScript.
+
+3. Should we commit baseline outputs?
+   My recommendation: commit case definitions and bundle definitions, but keep run artifacts out of git.
+
+4. Should we add hosted experiment tracking immediately?
+   My recommendation: no. Revisit after the local harness proves useful.
+
+## Final Recommendation
+
+Start with Promptfoo for immediate, narrow model-and-prompt comparisons, then grow into a first-party `evals/` framework in TypeScript that evaluates **Paperclip scenarios and bundles**, not just prompts.
+
+Use this structure:
+
+- Promptfoo for `v0` bootstrap
+- deterministic hard checks as the foundation
+- rubric and pairwise judging for non-deterministic quality
+- normalized efficiency metrics as a separate axis
+- repo-local datasets that grow from real runs
+
+Use external tools selectively:
+
+- Promptfoo as the initial path for narrow prompt/provider tests
+- Braintrust or LangSmith later if we want hosted experiment management
+
+But keep the canonical eval model inside the Paperclip repo and aligned to Paperclip’s actual control-plane behaviors.

doc/plans/2026-03-13-paperclip-skill-tightening-plan.md

@@ -0,0 +1,186 @@
+# Paperclip Skill Tightening Plan
+
+## Status
+
+Deferred follow-up. Do not include in the current token-optimization PR beyond documenting the plan.
+
+## Why This Is Deferred
+
+The `paperclip` skill is part of the critical control-plane safety surface. Tightening it may reduce fresh-session token use, but it also carries prompt-regression risk. We do not yet have evals that would let us safely prove behavior preservation across assignment handling, checkout rules, comment etiquette, approval workflows, and escalation paths.
+
+The current PR should ship the lower-risk infrastructure wins first:
+
+- telemetry normalization
+- safe session reuse
+- incremental issue/comment context
+- bootstrap versus heartbeat prompt separation
+- Codex worktree isolation
+
+## Current Problem
+
+Fresh runs still spend substantial input tokens even after the context-path fixes. The remaining large startup cost appears to come from loading the full `paperclip` skill and related instruction surface into context at run start.
+
+The skill currently mixes three kinds of content in one file:
+
+- hot-path heartbeat procedure used on nearly every run
+- critical policy and safety invariants
+- rare workflow/reference material that most runs do not need
+
+That structure is safe but expensive.
+
+## Goals
+
+- reduce first-run instruction tokens without weakening agent safety
+- preserve all current Paperclip control-plane capabilities
+- keep common heartbeat behavior explicit and easy for agents to follow
+- move rare workflows and reference material out of the hot path
+- create a structure that can later be evaluated systematically
+
+## Non-Goals
+
+- changing Paperclip API semantics
+- removing required governance rules
+- deleting rare workflows
+- changing agent defaults in the current PR
+
+## Recommended Direction
+
+### 1. Split Hot Path From Lookup Material
+
+Restructure the skill into:
+
+- an always-loaded core section for the common heartbeat loop
+- on-demand material for infrequent workflows and deep reference
+
+The core should cover only what is needed on nearly every wake:
+
+- auth and required headers
+- inbox-first assignment retrieval
+- mandatory checkout behavior
+- `heartbeat-context` first
+- incremental comment retrieval rules
+- mention/self-assign exception
+- blocked-task dedup
+- status/comment/release expectations before exit
+
+### 2. Normalize The Skill Around One Canonical Procedure
+
+The same rules are currently expressed multiple times across:
+
+- heartbeat steps
+- critical rules
+- endpoint reference
+- workflow examples
+
+Refactor so each operational fact has one primary home:
+
+- procedure
+- invariant list
+- appendix/reference
+
+This reduces prompt weight and lowers the chance of internal instruction drift.
+
+### 3. Compress Prose Into High-Signal Instruction Forms
+
+Rewrite the hot path using compact operational forms:
+
+- short ordered checklist
+- flat invariant list
+- minimal examples only where ambiguity would be risky
+
+Reduce:
+
+- narrative explanation
+- repeated warnings already covered elsewhere
+- large example payloads for common operations
+- long endpoint matrices in the main body
+
+### 4. Move Rare Workflows Behind Explicit Triggers
+
+These workflows should remain available but should not dominate fresh-run context:
+
+- OpenClaw invite flow
+- project setup flow
+- planning `<plan/>` writeback flow
+- instructions-path update flow
+- detailed link-formatting examples
+
+Recommended approach:
+
+- keep a short pointer in the main skill
+- move detailed procedures into sibling skills or referenced docs that agents read only when needed
+
+### 5. Separate Policy From Reference
+
+The skill should distinguish:
+
+- mandatory operating rules
+- endpoint lookup/reference
+- business-process playbooks
+
+That separation makes it easier to evaluate prompt changes later and lets adapters or orchestration choose what must always be loaded.
+
+## Proposed Target Structure
+
+1. Purpose and authentication
+2. Compact heartbeat procedure
+3. Hard invariants
+4. Required comment/update style
+5. Triggered workflow index
+6. Appendix/reference
+
+## Rollout Plan
+
+### Phase 1. Inventory And Measure
+
+- annotate the current skill by section and estimate token weight
+- identify which sections are truly hot-path versus rare
+- capture representative runs to compare before/after prompt size and behavior
+
+### Phase 2. Structural Refactor Without Semantic Changes
+
+- rewrite the main skill into the target structure
+- preserve all existing rules and capabilities
+- move rare workflow details into referenced companion material
+- keep wording changes conservative
+
+### Phase 3. Validate Against Real Scenarios
+
+Run scenario checks for:
+
+- normal assigned heartbeat
+- comment-triggered wake
+- blocked-task dedup behavior
+- approval-resolution wake
+- delegation/subtask creation
+- board handoff back to user
+- plan-request handling
+
+### Phase 4. Decide Default Loading Strategy
+
+After validation, decide whether:
+
+- the entire main skill still loads by default, or
+- only the compact core loads by default and rare sections are fetched on demand
+
+Do not change this loading policy without validation.
+
+## Risks
+
+- prompt degradation on control-plane safety rules
+- agents forgetting rare but important workflows
+- accidental removal of repeated wording that was carrying useful behavior
+- introducing ambiguous instruction precedence between the core skill and companion materials
+
+## Preconditions Before Implementation
+
+- define acceptance scenarios for control-plane correctness
+- add at least lightweight eval or scripted scenario coverage for key Paperclip flows
+- confirm how adapter/bootstrap layering should load skill content versus references
+
+## Success Criteria
+
+- materially lower first-run input tokens for Paperclip-coordinated agents
+- no regression in checkout discipline, issue updates, blocked handling, or delegation
+- no increase in malformed API usage or ownership mistakes
+- agents still complete rare workflows correctly when explicitly asked

docs/adapters/codex-local.md

@@ -30,6 +30,8 @@ Codex uses `previous_response_id` for session continuity. The adapter serializes
 
 The adapter symlinks Paperclip skills into the global Codex skills directory (`~/.codex/skills`). Existing user skills are not overwritten.
 
+When Paperclip is running inside a managed worktree instance (`PAPERCLIP_IN_WORKTREE=true`), the adapter instead uses a worktree-isolated `CODEX_HOME` under the Paperclip instance so Codex skills, sessions, logs, and other runtime state do not leak across checkouts. It seeds that isolated home from the user's main Codex home for shared auth/config continuity.
+
 For manual local CLI usage outside heartbeat runs (for example running as `codexcoder` directly), use:
 
 ```sh

docs/adapters/creating-an-adapter.md

@@ -6,7 +6,7 @@ summary: Guide to building a custom adapter
 Build a custom adapter to connect Paperclip to any agent runtime.
 
 <Tip>
-If you're using Claude Code, the `create-agent-adapter` skill can guide you through the full adapter creation process interactively. Just ask Claude to create a new adapter and it will walk you through each step.
+If you're using Claude Code, the `.agents/skills/create-agent-adapter` skill can guide you through the full adapter creation process interactively. Just ask Claude to create a new adapter and it will walk you through each step.
 </Tip>
 
 ## Package Structure

docs/api/issues.md

@@ -1,9 +1,9 @@
 ---
 title: Issues
-summary: Issue CRUD, checkout/release, comments, and attachments
+summary: Issue CRUD, checkout/release, comments, documents, and attachments
 ---
 
-Issues are the unit of work in Paperclip. They support hierarchical relationships, atomic checkout, comments, and file attachments.
+Issues are the unit of work in Paperclip. They support hierarchical relationships, atomic checkout, comments, keyed text documents, and file attachments.
 
 ## List Issues
 
@@ -29,6 +29,12 @@ GET /api/issues/{issueId}
 
 Returns the issue with `project`, `goal`, and `ancestors` (parent chain with their projects and goals).
 
+The response also includes:
+
+- `planDocument`: the full text of the issue document with key `plan`, when present
+- `documentSummaries`: metadata for all linked issue documents
+- `legacyPlanDocument`: a read-only fallback when the description still contains an old `<plan>` block
+
 ## Create Issue
 
 ```
@@ -100,6 +106,54 @@ POST /api/issues/{issueId}/comments
 
 @-mentions (`@AgentName`) in comments trigger heartbeats for the mentioned agent.
 
+## Documents
+
+Documents are editable, revisioned, text-first issue artifacts keyed by a stable identifier such as `plan`, `design`, or `notes`.
+
+### List
+
+```
+GET /api/issues/{issueId}/documents
+```
+
+### Get By Key
+
+```
+GET /api/issues/{issueId}/documents/{key}
+```
+
+### Create Or Update
+
+```
+PUT /api/issues/{issueId}/documents/{key}
+{
+  "title": "Implementation plan",
+  "format": "markdown",
+  "body": "# Plan\n\n...",
+  "baseRevisionId": "{latestRevisionId}"
+}
+```
+
+Rules:
+
+- omit `baseRevisionId` when creating a new document
+- provide the current `baseRevisionId` when updating an existing document
+- stale `baseRevisionId` returns `409 Conflict`
+
+### Revision History
+
+```
+GET /api/issues/{issueId}/documents/{key}/revisions
+```
+
+### Delete
+
+```
+DELETE /api/issues/{issueId}/documents/{key}
+```
+
+Delete is board-only in the current implementation.
+
 ## Attachments
 
 ### Upload

docs/plans/2026-03-13-issue-documents-plan.md

@@ -0,0 +1,569 @@
+# Issue Documents Plan
+
+Status: Draft  
+Owner: Backend + UI + Agent Protocol  
+Date: 2026-03-13  
+Primary issue: `PAP-448`
+
+## Summary
+
+Add first-class **documents** to Paperclip as editable, revisioned, company-scoped text artifacts that can be linked to issues.
+
+The first required convention is a document with key `plan`.
+
+This solves the immediate workflow problem in `PAP-448`:
+
+- plans should stop living inside issue descriptions as `<plan>` blocks
+- agents and board users should be able to create/update issue documents directly
+- `GET /api/issues/:id` should include the full `plan` document and expose the other available documents
+- issue detail should render documents under the description
+
+This should be built as the **text-document slice** of the broader artifact system, not as a replacement for attachments/assets.
+
+## Recommended Product Shape
+
+### Documents vs attachments vs artifacts
+
+- **Documents**: editable text content with stable keys and revision history.
+- **Attachments**: uploaded/generated opaque files backed by storage (`assets` + `issue_attachments`).
+- **Artifacts**: later umbrella/read-model that can unify documents, attachments, previews, and workspace files.
+
+Recommendation:
+
+- implement **issue documents now**
+- keep existing attachments as-is
+- defer full artifact unification until there is a second real consumer beyond issue documents + attachments
+
+This keeps `PAP-448` focused while still fitting the larger artifact direction.
+
+## Goals
+
+1. Give issues first-class keyed documents, starting with `plan`.
+2. Make documents editable by board users and same-company agents with issue access.
+3. Preserve change history with append-only revisions.
+4. Make the `plan` document automatically available in the normal issue fetch used by agents/heartbeats.
+5. Replace the current `<plan>`-in-description convention in skills/docs.
+6. Keep the design compatible with a future artifact/deliverables layer.
+
+## Non-Goals
+
+- full collaborative doc editing
+- binary-file version history
+- browser IDE or workspace editor
+- full artifact-system implementation in the same change
+- generalized polymorphic relations for every entity type on day one
+
+## Product Decisions
+
+### 1. Keyed issue documents
+
+Each issue can have multiple documents. Each document relation has a stable key:
+
+- `plan`
+- `design`
+- `notes`
+- `report`
+- custom keys later
+
+Key rules:
+
+- unique per issue, case-insensitive
+- normalized to lowercase slug form
+- machine-oriented and stable
+- title is separate and user-facing
+
+The `plan` key is conventional and reserved by Paperclip workflow/docs.
+
+### 2. Text-first v1
+
+V1 documents should be text-first, not arbitrary blobs.
+
+Recommended supported formats:
+
+- `markdown`
+- `plain_text`
+- `json`
+- `html`
+
+Recommendation:
+
+- optimize UI for `markdown`
+- allow raw editing for the others
+- keep PDFs/images/CSVs/etc as attachments/artifacts, not editable documents
+
+### 3. Revision model
+
+Every document update creates a new immutable revision.
+
+The current document row stores the latest snapshot for fast reads.
+
+### 4. Concurrency model
+
+Do not use silent last-write-wins.
+
+Updates should include `baseRevisionId`:
+
+- create: no base revision required
+- update: `baseRevisionId` must match current latest revision
+- mismatch: return `409 Conflict`
+
+This is important because both board users and agents may edit the same document.
+
+### 5. Issue fetch behavior
+
+`GET /api/issues/:id` should include:
+
+- full `planDocument` when a `plan` document exists
+- `documentSummaries` for all linked documents
+
+It should not inline every document body by default.
+
+This keeps issue fetches useful for agents without making every issue payload unbounded.
+
+### 6. Legacy `<plan>` compatibility
+
+If an issue has no `plan` document but its description contains a legacy `<plan>` block:
+
+- expose that as a legacy read-only fallback in API/UI
+- mark it as legacy/synthetic
+- prefer a real `plan` document when both exist
+
+Recommendation:
+
+- do not auto-rewrite old issue descriptions in the first rollout
+- provide an explicit import/migrate path later
+
+## Proposed Data Model
+
+Recommendation: make documents first-class, but keep issue linkage explicit via a join table.
+
+This preserves foreign keys today and gives a clean path to future `project_documents` or `company_documents` tables later.
+
+## Tables
+
+### `documents`
+
+Canonical text document record.
+
+Suggested columns:
+
+- `id`
+- `company_id`
+- `title`
+- `format`
+- `latest_body`
+- `latest_revision_id`
+- `latest_revision_number`
+- `created_by_agent_id`
+- `created_by_user_id`
+- `updated_by_agent_id`
+- `updated_by_user_id`
+- `created_at`
+- `updated_at`
+
+### `document_revisions`
+
+Append-only history.
+
+Suggested columns:
+
+- `id`
+- `company_id`
+- `document_id`
+- `revision_number`
+- `body`
+- `change_summary`
+- `created_by_agent_id`
+- `created_by_user_id`
+- `created_at`
+
+Constraints:
+
+- unique `(document_id, revision_number)`
+
+### `issue_documents`
+
+Issue relation + workflow key.
+
+Suggested columns:
+
+- `id`
+- `company_id`
+- `issue_id`
+- `document_id`
+- `key`
+- `created_at`
+- `updated_at`
+
+Constraints:
+
+- unique `(company_id, issue_id, key)`
+- unique `(document_id)` to keep one issue relation per document in v1
+
+## Why not use `assets` for this?
+
+Because `assets` solves blob storage, not:
+
+- stable keyed semantics like `plan`
+- inline text editing
+- revision history
+- optimistic concurrency
+- cheap inclusion in `GET /issues/:id`
+
+Documents and attachments should remain separate primitives, then meet later in a deliverables/artifact read-model.
+
+## Shared Types and API Contract
+
+## New shared types
+
+Add:
+
+- `DocumentFormat`
+- `IssueDocument`
+- `IssueDocumentSummary`
+- `DocumentRevision`
+
+Recommended `IssueDocument` shape:
+
+```ts
+type DocumentFormat = "markdown" | "plain_text" | "json" | "html";
+
+interface IssueDocument {
+  id: string;
+  companyId: string;
+  issueId: string;
+  key: string;
+  title: string | null;
+  format: DocumentFormat;
+  body: string;
+  latestRevisionId: string;
+  latestRevisionNumber: number;
+  createdByAgentId: string | null;
+  createdByUserId: string | null;
+  updatedByAgentId: string | null;
+  updatedByUserId: string | null;
+  createdAt: Date;
+  updatedAt: Date;
+}
+```
+
+Recommended `IssueDocumentSummary` shape:
+
+```ts
+interface IssueDocumentSummary {
+  id: string;
+  key: string;
+  title: string | null;
+  format: DocumentFormat;
+  latestRevisionId: string;
+  latestRevisionNumber: number;
+  updatedAt: Date;
+}
+```
+
+## Issue type enrichment
+
+Extend `Issue` with:
+
+```ts
+interface Issue {
+  ...
+  planDocument?: IssueDocument | null;
+  documentSummaries?: IssueDocumentSummary[];
+  legacyPlanDocument?: {
+    key: "plan";
+    body: string;
+    source: "issue_description";
+  } | null;
+}
+```
+
+This directly satisfies the `PAP-448` requirement for heartbeat/API issue fetches.
+
+## API endpoints
+
+Recommended endpoints:
+
+- `GET /api/issues/:issueId/documents`
+- `GET /api/issues/:issueId/documents/:key`
+- `PUT /api/issues/:issueId/documents/:key`
+- `GET /api/issues/:issueId/documents/:key/revisions`
+- `DELETE /api/issues/:issueId/documents/:key` optionally board-only in v1
+
+Recommended `PUT` body:
+
+```ts
+{
+  title?: string | null;
+  format: "markdown" | "plain_text" | "json" | "html";
+  body: string;
+  changeSummary?: string | null;
+  baseRevisionId?: string | null;
+}
+```
+
+Behavior:
+
+- missing document + no `baseRevisionId`: create
+- existing document + matching `baseRevisionId`: update
+- existing document + stale `baseRevisionId`: `409`
+
+## Authorization and invariants
+
+- all document records are company-scoped
+- issue relation must belong to same company
+- board access follows existing issue access rules
+- agent access follows existing same-company issue access rules
+- every mutation writes activity log entries
+
+Recommended delete rule for v1:
+
+- board can delete documents
+- agents can create/update, but not delete
+
+That keeps automated systems from removing canonical docs too easily.
+
+## UI Plan
+
+## Issue detail
+
+Add a new **Documents** section directly under the issue description.
+
+Recommended behavior:
+
+- show `plan` first when present
+- show other documents below it
+- render a gist-like header:
+  - key
+  - title
+  - last updated metadata
+  - revision number
+- support inline edit
+- support create new document by key
+- support revision history drawer or sheet
+
+Recommended presentation order:
+
+1. Description
+2. Documents
+3. Attachments
+4. Comments / activity / sub-issues
+
+This matches the request that documents live under the description while still leaving attachments available.
+
+## Editing UX
+
+Recommendation:
+
+- use markdown preview + raw edit toggle for markdown docs
+- use raw textarea editor for non-markdown docs in v1
+- show explicit save conflicts on `409`
+- show a clear empty state: "No documents yet"
+
+## Legacy plan rendering
+
+If there is no stored `plan` document but legacy `<plan>` exists:
+
+- show it in the Documents section
+- mark it `Legacy plan from description`
+- offer create/import in a later pass
+
+## Agent Protocol and Skills
+
+Update the Paperclip agent workflow so planning no longer edits the issue description.
+
+Required changes:
+
+- update `skills/paperclip/SKILL.md`
+- replace the `<plan>` instructions with document creation/update instructions
+- document the new endpoints in `docs/api/issues.md`
+- update any internal planning docs that still teach inline `<plan>` blocks
+
+New rule:
+
+- when asked to make a plan for an issue, create or update the issue document with key `plan`
+- leave a comment that the plan document was created/updated
+- do not mark the issue done
+
+## Relationship to the Artifact Plan
+
+This work should explicitly feed the broader artifact/deliverables direction.
+
+Recommendation:
+
+- keep documents as their own primitive in this change
+- add `document` to any future `ArtifactKind`
+- later build a deliverables read-model that aggregates:
+  - issue documents
+  - issue attachments
+  - preview URLs
+  - workspace-file references
+
+The artifact proposal currently has no explicit `document` kind. It should.
+
+Recommended future shape:
+
+```ts
+type ArtifactKind =
+  | "document"
+  | "attachment"
+  | "workspace_file"
+  | "preview"
+  | "report_link";
+```
+
+## Implementation Phases
+
+## Phase 1: Shared contract and schema
+
+Files:
+
+- `packages/db/src/schema/documents.ts`
+- `packages/db/src/schema/document_revisions.ts`
+- `packages/db/src/schema/issue_documents.ts`
+- `packages/db/src/schema/index.ts`
+- `packages/db/src/migrations/*`
+- `packages/shared/src/types/issue.ts`
+- `packages/shared/src/validators/issue.ts` or new document validator file
+- `packages/shared/src/index.ts`
+
+Acceptance:
+
+- schema enforces one key per issue
+- revisions are append-only
+- shared types expose plan/document fields on issue fetch
+
+## Phase 2: Server services and routes
+
+Files:
+
+- `server/src/services/issues.ts` or `server/src/services/documents.ts`
+- `server/src/routes/issues.ts`
+- `server/src/services/activity.ts` callsites
+
+Behavior:
+
+- list/get/upsert/delete documents
+- revision listing
+- `GET /issues/:id` returns `planDocument` + `documentSummaries`
+- company boundary checks match issue routes
+
+Acceptance:
+
+- agents and board can fetch/update same-company issue documents
+- stale edits return `409`
+- activity timeline shows document changes
+
+## Phase 3: UI issue documents surface
+
+Files:
+
+- `ui/src/api/issues.ts`
+- `ui/src/lib/queryKeys.ts`
+- `ui/src/pages/IssueDetail.tsx`
+- new reusable document UI component if needed
+
+Behavior:
+
+- render plan + documents under description
+- create/update by key
+- open revision history
+- show conflicts/errors clearly
+
+Acceptance:
+
+- board can create a `plan` doc from issue detail
+- updated plan appears immediately
+- issue detail no longer depends on description-embedded `<plan>`
+
+## Phase 4: Skills/docs migration
+
+Files:
+
+- `skills/paperclip/SKILL.md`
+- `docs/api/issues.md`
+- `doc/SPEC-implementation.md`
+- relevant plan/docs that mention `<plan>`
+
+Acceptance:
+
+- planning guidance references issue documents, not inline issue description tags
+- API docs describe the new document endpoints and issue payload additions
+
+## Phase 5: Legacy compatibility and follow-up
+
+Behavior:
+
+- read legacy `<plan>` blocks as fallback
+- optionally add explicit import/migration command later
+
+Follow-up, not required for first merge:
+
+- deliverables/artifact read-model
+- project/company documents
+- comment-linked documents
+- diff view between revisions
+
+## Test Plan
+
+### Server
+
+- document create/read/update/delete lifecycle
+- revision numbering
+- `baseRevisionId` conflict handling
+- company boundary enforcement
+- agent vs board authorization
+- issue fetch includes `planDocument` and document summaries
+- legacy `<plan>` fallback behavior
+- activity log mutation coverage
+
+### UI
+
+- issue detail shows plan document
+- create/update flows invalidate queries correctly
+- conflict and validation errors are surfaced
+- legacy plan fallback renders correctly
+
+### Verification
+
+Run before implementation is declared complete:
+
+```sh
+pnpm -r typecheck
+pnpm test:run
+pnpm build
+```
+
+## Open Questions
+
+1. Should v1 documents be markdown-only, with `json/html/plain_text` deferred?
+   Recommendation: allow all four in API, optimize UI for markdown only.
+
+2. Should agents be allowed to create arbitrary keys, or only conventional keys?
+   Recommendation: allow arbitrary keys with normalized validation; reserve `plan` as special behavior only.
+
+3. Should delete exist in v1?
+   Recommendation: yes, but board-only.
+
+4. Should legacy `<plan>` blocks ever be auto-migrated?
+   Recommendation: no automatic mutation in the first rollout.
+
+5. Should documents appear inside a future Deliverables section or remain a top-level Issue section?
+   Recommendation: keep a dedicated Documents section now; later also expose them in Deliverables if an aggregated artifact view is added.
+
+## Final Recommendation
+
+Ship **issue documents** as a focused, text-first primitive now.
+
+Do not try to solve full artifact unification in the same implementation.
+
+Use:
+
+- first-class document tables
+- issue-level keyed linkage
+- append-only revisions
+- `planDocument` embedded in normal issue fetches
+- legacy `<plan>` fallback
+- skill/docs migration away from description-embedded plans
+
+This addresses the real planning workflow problem immediately and leaves the artifact system room to grow cleanly afterward.

packages/adapter-utils/src/server-utils.ts

@@ -112,6 +112,16 @@ export function renderTemplate(template: string, data: Record<string, unknown>)
   return template.replace(/{{\s*([a-zA-Z0-9_.-]+)\s*}}/g, (_, path) => resolvePathValue(data, path));
 }
 
+export function joinPromptSections(
+  sections: Array<string | null | undefined>,
+  separator = "\n\n",
+) {
+  return sections
+    .map((value) => (typeof value === "string" ? value.trim() : ""))
+    .filter(Boolean)
+    .join(separator);
+}
+
 export function redactEnvForLogs(env: Record<string, string>): Record<string, string> {
   const redacted: Record<string, string> = {};
   for (const [key, value] of Object.entries(env)) {

packages/adapter-utils/src/types.ts

@@ -99,6 +99,7 @@ export interface AdapterInvocationMeta {
   commandNotes?: string[];
   env?: Record<string, string>;
   prompt?: string;
+  promptMetrics?: Record<string, number>;
   context?: Record<string, unknown>;
 }
 

packages/adapters/claude-local/src/server/execute.ts

@@ -12,6 +12,7 @@ import {
   parseObject,
   parseJson,
   buildPaperclipEnv,
+  joinPromptSections,
   redactEnvForLogs,
   ensureAbsoluteDirectory,
   ensureCommandResolvable,
@@ -363,7 +364,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
       `[paperclip] Claude session "${runtimeSessionId}" was saved for cwd "${runtimeSessionCwd}" and will not be resumed in "${cwd}".\n`,
     );
   }
-  const prompt = renderTemplate(promptTemplate, {
+  const bootstrapPromptTemplate = asString(config.bootstrapPromptTemplate, "");
+  const templateData = {
     agentId: agent.id,
     companyId: agent.companyId,
     runId,
@@ -371,7 +373,24 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     agent,
     run: { id: runId, source: "on_demand" },
     context,
-  });
+  };
+  const renderedPrompt = renderTemplate(promptTemplate, templateData);
+  const renderedBootstrapPrompt =
+    !sessionId && bootstrapPromptTemplate.trim().length > 0
+      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
+      : "";
+  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
+  const prompt = joinPromptSections([
+    renderedBootstrapPrompt,
+    sessionHandoffNote,
+    renderedPrompt,
+  ]);
+  const promptMetrics = {
+    promptChars: prompt.length,
+    bootstrapPromptChars: renderedBootstrapPrompt.length,
+    sessionHandoffChars: sessionHandoffNote.length,
+    heartbeatPromptChars: renderedPrompt.length,
+  };
 
   const buildClaudeArgs = (resumeSessionId: string | null) => {
     const args = ["--print", "-", "--output-format", "stream-json", "--verbose"];
@@ -416,6 +435,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         commandNotes,
         env: redactEnvForLogs(env),
         prompt,
+        promptMetrics,
         context,
       });
     }

packages/adapters/claude-local/src/ui/build-config.ts

@@ -67,6 +67,7 @@ export function buildClaudeLocalConfig(v: CreateConfigValues): Record<string, un
   if (v.cwd) ac.cwd = v.cwd;
   if (v.instructionsFilePath) ac.instructionsFilePath = v.instructionsFilePath;
   if (v.promptTemplate) ac.promptTemplate = v.promptTemplate;
+  if (v.bootstrapPrompt) ac.bootstrapPromptTemplate = v.bootstrapPrompt;
   if (v.model) ac.model = v.model;
   if (v.thinkingEffort) ac.effort = v.thinkingEffort;
   if (v.chrome) ac.chrome = true;

packages/adapters/codex-local/src/server/codex-home.ts

@@ -0,0 +1,101 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+import type { AdapterExecutionContext } from "@paperclipai/adapter-utils";
+
+const TRUTHY_ENV_RE = /^(1|true|yes|on)$/i;
+const COPIED_SHARED_FILES = ["config.json", "config.toml", "instructions.md"] as const;
+const SYMLINKED_SHARED_FILES = ["auth.json"] as const;
+
+function nonEmpty(value: string | undefined): string | null {
+  return typeof value === "string" && value.trim().length > 0 ? value.trim() : null;
+}
+
+export async function pathExists(candidate: string): Promise<boolean> {
+  return fs.access(candidate).then(() => true).catch(() => false);
+}
+
+export function resolveCodexHomeDir(env: NodeJS.ProcessEnv = process.env): string {
+  const fromEnv = nonEmpty(env.CODEX_HOME);
+  if (fromEnv) return path.resolve(fromEnv);
+  return path.join(os.homedir(), ".codex");
+}
+
+function isWorktreeMode(env: NodeJS.ProcessEnv): boolean {
+  return TRUTHY_ENV_RE.test(env.PAPERCLIP_IN_WORKTREE ?? "");
+}
+
+function resolveWorktreeCodexHomeDir(env: NodeJS.ProcessEnv): string | null {
+  if (!isWorktreeMode(env)) return null;
+  const paperclipHome = nonEmpty(env.PAPERCLIP_HOME);
+  if (!paperclipHome) return null;
+  const instanceId = nonEmpty(env.PAPERCLIP_INSTANCE_ID);
+  if (instanceId) {
+    return path.resolve(paperclipHome, "instances", instanceId, "codex-home");
+  }
+  return path.resolve(paperclipHome, "codex-home");
+}
+
+async function ensureParentDir(target: string): Promise<void> {
+  await fs.mkdir(path.dirname(target), { recursive: true });
+}
+
+async function ensureSymlink(target: string, source: string): Promise<void> {
+  const existing = await fs.lstat(target).catch(() => null);
+  if (!existing) {
+    await ensureParentDir(target);
+    await fs.symlink(source, target);
+    return;
+  }
+
+  if (!existing.isSymbolicLink()) {
+    return;
+  }
+
+  const linkedPath = await fs.readlink(target).catch(() => null);
+  if (!linkedPath) return;
+
+  const resolvedLinkedPath = path.resolve(path.dirname(target), linkedPath);
+  if (resolvedLinkedPath === source) return;
+
+  await fs.unlink(target);
+  await fs.symlink(source, target);
+}
+
+async function ensureCopiedFile(target: string, source: string): Promise<void> {
+  const existing = await fs.lstat(target).catch(() => null);
+  if (existing) return;
+  await ensureParentDir(target);
+  await fs.copyFile(source, target);
+}
+
+export async function prepareWorktreeCodexHome(
+  env: NodeJS.ProcessEnv,
+  onLog: AdapterExecutionContext["onLog"],
+): Promise<string | null> {
+  const targetHome = resolveWorktreeCodexHomeDir(env);
+  if (!targetHome) return null;
+
+  const sourceHome = resolveCodexHomeDir(env);
+  if (path.resolve(sourceHome) === path.resolve(targetHome)) return targetHome;
+
+  await fs.mkdir(targetHome, { recursive: true });
+
+  for (const name of SYMLINKED_SHARED_FILES) {
+    const source = path.join(sourceHome, name);
+    if (!(await pathExists(source))) continue;
+    await ensureSymlink(path.join(targetHome, name), source);
+  }
+
+  for (const name of COPIED_SHARED_FILES) {
+    const source = path.join(sourceHome, name);
+    if (!(await pathExists(source))) continue;
+    await ensureCopiedFile(path.join(targetHome, name), source);
+  }
+
+  await onLog(
+    "stderr",
+    `[paperclip] Using worktree-isolated Codex home "${targetHome}" (seeded from "${sourceHome}").\n`,
+  );
+  return targetHome;
+}

packages/adapters/codex-local/src/server/execute.ts

@@ -1,5 +1,4 @@
 import fs from "node:fs/promises";
-import os from "node:os";
 import path from "node:path";
 import { fileURLToPath } from "node:url";
 import type { AdapterExecutionContext, AdapterExecutionResult } from "@paperclipai/adapter-utils";
@@ -18,9 +17,11 @@ import {
   listPaperclipSkillEntries,
   removeMaintainerOnlySkillSymlinks,
   renderTemplate,
+  joinPromptSections,
   runChildProcess,
 } from "@paperclipai/adapter-utils/server-utils";
 import { parseCodexJsonl, isCodexUnknownSessionError } from "./parse.js";
+import { pathExists, prepareWorktreeCodexHome, resolveCodexHomeDir } from "./codex-home.js";
 
 const __moduleDir = path.dirname(fileURLToPath(import.meta.url));
 const CODEX_ROLLOUT_NOISE_RE =
@@ -60,10 +61,32 @@ function resolveCodexBillingType(env: Record<string, string>): "api" | "subscrip
   return hasNonEmptyEnvValue(env, "OPENAI_API_KEY") ? "api" : "subscription";
 }
 
-function codexHomeDir(): string {
-  const fromEnv = process.env.CODEX_HOME;
-  if (typeof fromEnv === "string" && fromEnv.trim().length > 0) return fromEnv.trim();
-  return path.join(os.homedir(), ".codex");
+async function isLikelyPaperclipRepoRoot(candidate: string): Promise<boolean> {
+  const [hasWorkspace, hasPackageJson, hasServerDir, hasAdapterUtilsDir] = await Promise.all([
+    pathExists(path.join(candidate, "pnpm-workspace.yaml")),
+    pathExists(path.join(candidate, "package.json")),
+    pathExists(path.join(candidate, "server")),
+    pathExists(path.join(candidate, "packages", "adapter-utils")),
+  ]);
+
+  return hasWorkspace && hasPackageJson && hasServerDir && hasAdapterUtilsDir;
+}
+
+async function isLikelyPaperclipRuntimeSkillSource(candidate: string, skillName: string): Promise<boolean> {
+  if (path.basename(candidate) !== skillName) return false;
+  const skillsRoot = path.dirname(candidate);
+  if (path.basename(skillsRoot) !== "skills") return false;
+  if (!(await pathExists(path.join(candidate, "SKILL.md")))) return false;
+
+  let cursor = path.dirname(skillsRoot);
+  for (let depth = 0; depth < 6; depth += 1) {
+    if (await isLikelyPaperclipRepoRoot(cursor)) return true;
+    const parent = path.dirname(cursor);
+    if (parent === cursor) break;
+    cursor = parent;
+  }
+
+  return false;
 }
 
 type EnsureCodexSkillsInjectedOptions = {
@@ -79,7 +102,7 @@ export async function ensureCodexSkillsInjected(
   const skillsEntries = options.skillsEntries ?? await listPaperclipSkillEntries(__moduleDir);
   if (skillsEntries.length === 0) return;
 
-  const skillsHome = options.skillsHome ?? path.join(codexHomeDir(), "skills");
+  const skillsHome = options.skillsHome ?? path.join(resolveCodexHomeDir(process.env), "skills");
   await fs.mkdir(skillsHome, { recursive: true });
   const removedSkills = await removeMaintainerOnlySkillSymlinks(
     skillsHome,
@@ -96,6 +119,31 @@ export async function ensureCodexSkillsInjected(
     const target = path.join(skillsHome, entry.name);
 
     try {
+      const existing = await fs.lstat(target).catch(() => null);
+      if (existing?.isSymbolicLink()) {
+        const linkedPath = await fs.readlink(target).catch(() => null);
+        const resolvedLinkedPath = linkedPath
+          ? path.resolve(path.dirname(target), linkedPath)
+          : null;
+        if (
+          resolvedLinkedPath &&
+          resolvedLinkedPath !== entry.source &&
+          (await isLikelyPaperclipRuntimeSkillSource(resolvedLinkedPath, entry.name))
+        ) {
+          await fs.unlink(target);
+          if (linkSkill) {
+            await linkSkill(entry.source, target);
+          } else {
+            await fs.symlink(entry.source, target);
+          }
+          await onLog(
+            "stderr",
+            `[paperclip] Repaired Codex skill "${entry.name}" into ${skillsHome}\n`,
+          );
+          continue;
+        }
+      }
+
       const result = await ensurePaperclipSkillSymlink(entry.source, target, linkSkill);
       if (result === "skipped") continue;
 
@@ -160,12 +208,25 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
   const useConfiguredInsteadOfAgentHome = workspaceSource === "agent_home" && configuredCwd.length > 0;
   const effectiveWorkspaceCwd = useConfiguredInsteadOfAgentHome ? "" : workspaceCwd;
   const cwd = effectiveWorkspaceCwd || configuredCwd || process.cwd();
-  await ensureAbsoluteDirectory(cwd, { createIfMissing: true });
-  await ensureCodexSkillsInjected(onLog);
   const envConfig = parseObject(config.env);
+  const configuredCodexHome =
+    typeof envConfig.CODEX_HOME === "string" && envConfig.CODEX_HOME.trim().length > 0
+      ? path.resolve(envConfig.CODEX_HOME.trim())
+      : null;
+  await ensureAbsoluteDirectory(cwd, { createIfMissing: true });
+  const preparedWorktreeCodexHome =
+    configuredCodexHome ? null : await prepareWorktreeCodexHome(process.env, onLog);
+  const effectiveCodexHome = configuredCodexHome ?? preparedWorktreeCodexHome;
+  await ensureCodexSkillsInjected(
+    onLog,
+    effectiveCodexHome ? { skillsHome: path.join(effectiveCodexHome, "skills") } : {},
+  );
   const hasExplicitApiKey =
     typeof envConfig.PAPERCLIP_API_KEY === "string" && envConfig.PAPERCLIP_API_KEY.trim().length > 0;
   const env: Record<string, string> = { ...buildPaperclipEnv(agent) };
+  if (effectiveCodexHome) {
+    env.CODEX_HOME = effectiveCodexHome;
+  }
   env.PAPERCLIP_RUN_ID = runId;
   const wakeTaskId =
     (typeof context.taskId === "string" && context.taskId.trim().length > 0 && context.taskId.trim()) ||
@@ -278,6 +339,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
   const instructionsFilePath = asString(config.instructionsFilePath, "").trim();
   const instructionsDir = instructionsFilePath ? `${path.dirname(instructionsFilePath)}/` : "";
   let instructionsPrefix = "";
+  let instructionsChars = 0;
   if (instructionsFilePath) {
     try {
       const instructionsContents = await fs.readFile(instructionsFilePath, "utf8");
@@ -285,6 +347,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         `${instructionsContents}\n\n` +
         `The above agent instructions were loaded from ${instructionsFilePath}. ` +
         `Resolve any relative file references from ${instructionsDir}.\n\n`;
+      instructionsChars = instructionsPrefix.length;
       await onLog(
         "stderr",
         `[paperclip] Loaded agent instructions file: ${instructionsFilePath}\n`,
@@ -309,7 +372,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
       `Configured instructionsFilePath ${instructionsFilePath}, but file could not be read; continuing without injected instructions.`,
     ];
   })();
-  const renderedPrompt = renderTemplate(promptTemplate, {
+  const bootstrapPromptTemplate = asString(config.bootstrapPromptTemplate, "");
+  const templateData = {
     agentId: agent.id,
     companyId: agent.companyId,
     runId,
@@ -317,8 +381,26 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     agent,
     run: { id: runId, source: "on_demand" },
     context,
-  });
-  const prompt = `${instructionsPrefix}${renderedPrompt}`;
+  };
+  const renderedPrompt = renderTemplate(promptTemplate, templateData);
+  const renderedBootstrapPrompt =
+    !sessionId && bootstrapPromptTemplate.trim().length > 0
+      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
+      : "";
+  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
+  const prompt = joinPromptSections([
+    instructionsPrefix,
+    renderedBootstrapPrompt,
+    sessionHandoffNote,
+    renderedPrompt,
+  ]);
+  const promptMetrics = {
+    promptChars: prompt.length,
+    instructionsChars,
+    bootstrapPromptChars: renderedBootstrapPrompt.length,
+    sessionHandoffChars: sessionHandoffNote.length,
+    heartbeatPromptChars: renderedPrompt.length,
+  };
 
   const buildArgs = (resumeSessionId: string | null) => {
     const args = ["exec", "--json"];
@@ -346,6 +428,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         }),
         env: redactEnvForLogs(env),
         prompt,
+        promptMetrics,
         context,
       });
     }

packages/adapters/codex-local/src/ui/build-config.ts

@@ -71,6 +71,7 @@ export function buildCodexLocalConfig(v: CreateConfigValues): Record<string, unk
   if (v.cwd) ac.cwd = v.cwd;
   if (v.instructionsFilePath) ac.instructionsFilePath = v.instructionsFilePath;
   if (v.promptTemplate) ac.promptTemplate = v.promptTemplate;
+  if (v.bootstrapPrompt) ac.bootstrapPromptTemplate = v.bootstrapPrompt;
   ac.model = v.model || DEFAULT_CODEX_LOCAL_MODEL;
   if (v.thinkingEffort) ac.modelReasoningEffort = v.thinkingEffort;
   ac.timeoutSec = 0;

packages/adapters/cursor-local/src/server/execute.ts

@@ -17,6 +17,7 @@ import {
   listPaperclipSkillEntries,
   removeMaintainerOnlySkillSymlinks,
   renderTemplate,
+  joinPromptSections,
   runChildProcess,
 } from "@paperclipai/adapter-utils/server-utils";
 import { DEFAULT_CURSOR_LOCAL_MODEL } from "../index.js";
@@ -268,6 +269,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
   const instructionsFilePath = asString(config.instructionsFilePath, "").trim();
   const instructionsDir = instructionsFilePath ? `${path.dirname(instructionsFilePath)}/` : "";
   let instructionsPrefix = "";
+  let instructionsChars = 0;
   if (instructionsFilePath) {
     try {
       const instructionsContents = await fs.readFile(instructionsFilePath, "utf8");
@@ -275,6 +277,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         `${instructionsContents}\n\n` +
         `The above agent instructions were loaded from ${instructionsFilePath}. ` +
         `Resolve any relative file references from ${instructionsDir}.\n\n`;
+      instructionsChars = instructionsPrefix.length;
       await onLog(
         "stderr",
         `[paperclip] Loaded agent instructions file: ${instructionsFilePath}\n`,
@@ -307,7 +310,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     return notes;
   })();
 
-  const renderedPrompt = renderTemplate(promptTemplate, {
+  const bootstrapPromptTemplate = asString(config.bootstrapPromptTemplate, "");
+  const templateData = {
     agentId: agent.id,
     companyId: agent.companyId,
     runId,
@@ -315,9 +319,29 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     agent,
     run: { id: runId, source: "on_demand" },
     context,
-  });
+  };
+  const renderedPrompt = renderTemplate(promptTemplate, templateData);
+  const renderedBootstrapPrompt =
+    !sessionId && bootstrapPromptTemplate.trim().length > 0
+      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
+      : "";
+  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
   const paperclipEnvNote = renderPaperclipEnvNote(env);
-  const prompt = `${instructionsPrefix}${paperclipEnvNote}${renderedPrompt}`;
+  const prompt = joinPromptSections([
+    instructionsPrefix,
+    renderedBootstrapPrompt,
+    sessionHandoffNote,
+    paperclipEnvNote,
+    renderedPrompt,
+  ]);
+  const promptMetrics = {
+    promptChars: prompt.length,
+    instructionsChars,
+    bootstrapPromptChars: renderedBootstrapPrompt.length,
+    sessionHandoffChars: sessionHandoffNote.length,
+    runtimeNoteChars: paperclipEnvNote.length,
+    heartbeatPromptChars: renderedPrompt.length,
+  };
 
   const buildArgs = (resumeSessionId: string | null) => {
     const args = ["-p", "--output-format", "stream-json", "--workspace", cwd];
@@ -340,6 +364,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         commandArgs: args,
         env: redactEnvForLogs(env),
         prompt,
+        promptMetrics,
         context,
       });
     }

packages/adapters/cursor-local/src/ui/build-config.ts

@@ -62,6 +62,7 @@ export function buildCursorLocalConfig(v: CreateConfigValues): Record<string, un
   if (v.cwd) ac.cwd = v.cwd;
   if (v.instructionsFilePath) ac.instructionsFilePath = v.instructionsFilePath;
   if (v.promptTemplate) ac.promptTemplate = v.promptTemplate;
+  if (v.bootstrapPrompt) ac.bootstrapPromptTemplate = v.bootstrapPrompt;
   ac.model = v.model || DEFAULT_CURSOR_LOCAL_MODEL;
   const mode = normalizeMode(v.thinkingEffort);
   if (mode) ac.mode = mode;

packages/adapters/gemini-local/src/server/execute.ts

@@ -13,6 +13,7 @@ import {
   ensureAbsoluteDirectory,
   ensureCommandResolvable,
   ensurePaperclipSkillSymlink,
+  joinPromptSections,
   ensurePathInEnv,
   listPaperclipSkillEntries,
   removeMaintainerOnlySkillSymlinks,
@@ -268,7 +269,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     return notes;
   })();
 
-  const renderedPrompt = renderTemplate(promptTemplate, {
+  const bootstrapPromptTemplate = asString(config.bootstrapPromptTemplate, "");
+  const templateData = {
     agentId: agent.id,
     companyId: agent.companyId,
     runId,
@@ -276,10 +278,31 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     agent,
     run: { id: runId, source: "on_demand" },
     context,
-  });
+  };
+  const renderedPrompt = renderTemplate(promptTemplate, templateData);
+  const renderedBootstrapPrompt =
+    !sessionId && bootstrapPromptTemplate.trim().length > 0
+      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
+      : "";
+  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
   const paperclipEnvNote = renderPaperclipEnvNote(env);
   const apiAccessNote = renderApiAccessNote(env);
-  const prompt = `${instructionsPrefix}${paperclipEnvNote}${apiAccessNote}${renderedPrompt}`;
+  const prompt = joinPromptSections([
+    instructionsPrefix,
+    renderedBootstrapPrompt,
+    sessionHandoffNote,
+    paperclipEnvNote,
+    apiAccessNote,
+    renderedPrompt,
+  ]);
+  const promptMetrics = {
+    promptChars: prompt.length,
+    instructionsChars: instructionsPrefix.length,
+    bootstrapPromptChars: renderedBootstrapPrompt.length,
+    sessionHandoffChars: sessionHandoffNote.length,
+    runtimeNoteChars: paperclipEnvNote.length + apiAccessNote.length,
+    heartbeatPromptChars: renderedPrompt.length,
+  };
 
   const buildArgs = (resumeSessionId: string | null) => {
     const args = ["--output-format", "stream-json"];
@@ -309,6 +332,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         )),
         env: redactEnvForLogs(env),
         prompt,
+        promptMetrics,
         context,
       });
     }

packages/adapters/gemini-local/src/ui/build-config.ts

@@ -56,6 +56,7 @@ export function buildGeminiLocalConfig(v: CreateConfigValues): Record<string, un
   if (v.cwd) ac.cwd = v.cwd;
   if (v.instructionsFilePath) ac.instructionsFilePath = v.instructionsFilePath;
   if (v.promptTemplate) ac.promptTemplate = v.promptTemplate;
+  if (v.bootstrapPrompt) ac.bootstrapPromptTemplate = v.bootstrapPrompt;
   ac.model = v.model || DEFAULT_GEMINI_LOCAL_MODEL;
   ac.timeoutSec = 0;
   ac.graceSec = 15;

packages/adapters/opencode-local/src/server/execute.ts

@@ -9,6 +9,7 @@ import {
   asStringArray,
   parseObject,
   buildPaperclipEnv,
+  joinPromptSections,
   redactEnvForLogs,
   ensureAbsoluteDirectory,
   ensureCommandResolvable,
@@ -233,7 +234,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     ];
   })();
 
-  const renderedPrompt = renderTemplate(promptTemplate, {
+  const bootstrapPromptTemplate = asString(config.bootstrapPromptTemplate, "");
+  const templateData = {
     agentId: agent.id,
     companyId: agent.companyId,
     runId,
@@ -241,8 +243,26 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     agent,
     run: { id: runId, source: "on_demand" },
     context,
-  });
-  const prompt = `${instructionsPrefix}${renderedPrompt}`;
+  };
+  const renderedPrompt = renderTemplate(promptTemplate, templateData);
+  const renderedBootstrapPrompt =
+    !sessionId && bootstrapPromptTemplate.trim().length > 0
+      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
+      : "";
+  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
+  const prompt = joinPromptSections([
+    instructionsPrefix,
+    renderedBootstrapPrompt,
+    sessionHandoffNote,
+    renderedPrompt,
+  ]);
+  const promptMetrics = {
+    promptChars: prompt.length,
+    instructionsChars: instructionsPrefix.length,
+    bootstrapPromptChars: renderedBootstrapPrompt.length,
+    sessionHandoffChars: sessionHandoffNote.length,
+    heartbeatPromptChars: renderedPrompt.length,
+  };
 
   const buildArgs = (resumeSessionId: string | null) => {
     const args = ["run", "--format", "json"];
@@ -264,6 +284,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         commandArgs: [...args, `<stdin prompt ${prompt.length} chars>`],
         env: redactEnvForLogs(env),
         prompt,
+        promptMetrics,
         context,
       });
     }

packages/adapters/opencode-local/src/ui/build-config.ts

@@ -55,6 +55,7 @@ export function buildOpenCodeLocalConfig(v: CreateConfigValues): Record<string,
   if (v.cwd) ac.cwd = v.cwd;
   if (v.instructionsFilePath) ac.instructionsFilePath = v.instructionsFilePath;
   if (v.promptTemplate) ac.promptTemplate = v.promptTemplate;
+  if (v.bootstrapPrompt) ac.bootstrapPromptTemplate = v.bootstrapPrompt;
   if (v.model) ac.model = v.model;
   if (v.thinkingEffort) ac.variant = v.thinkingEffort;
   // OpenCode sessions can run until the CLI exits naturally; keep timeout disabled (0)

packages/adapters/pi-local/src/server/execute.ts

@@ -9,6 +9,7 @@ import {
   asStringArray,
   parseObject,
   buildPaperclipEnv,
+  joinPromptSections,
   redactEnvForLogs,
   ensureAbsoluteDirectory,
   ensureCommandResolvable,
@@ -270,7 +271,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     systemPromptExtension = promptTemplate;
   }
 
-  const renderedSystemPromptExtension = renderTemplate(systemPromptExtension, {
+  const bootstrapPromptTemplate = asString(config.bootstrapPromptTemplate, "");
+  const templateData = {
     agentId: agent.id,
     companyId: agent.companyId,
     runId,
@@ -278,18 +280,26 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     agent,
     run: { id: runId, source: "on_demand" },
     context,
-  });
-
-  // User prompt is simple - just the rendered prompt template without instructions
-  const userPrompt = renderTemplate(promptTemplate, {
-    agentId: agent.id,
-    companyId: agent.companyId,
-    runId,
-    company: { id: agent.companyId },
-    agent,
-    run: { id: runId, source: "on_demand" },
-    context,
-  });
+  };
+  const renderedSystemPromptExtension = renderTemplate(systemPromptExtension, templateData);
+  const renderedHeartbeatPrompt = renderTemplate(promptTemplate, templateData);
+  const renderedBootstrapPrompt =
+    !canResumeSession && bootstrapPromptTemplate.trim().length > 0
+      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
+      : "";
+  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
+  const userPrompt = joinPromptSections([
+    renderedBootstrapPrompt,
+    sessionHandoffNote,
+    renderedHeartbeatPrompt,
+  ]);
+  const promptMetrics = {
+    systemPromptChars: renderedSystemPromptExtension.length,
+    promptChars: userPrompt.length,
+    bootstrapPromptChars: renderedBootstrapPrompt.length,
+    sessionHandoffChars: sessionHandoffNote.length,
+    heartbeatPromptChars: renderedHeartbeatPrompt.length,
+  };
 
   const commandNotes = (() => {
     if (!resolvedInstructionsFilePath) return [] as string[];
@@ -345,6 +355,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         commandArgs: args,
         env: redactEnvForLogs(env),
         prompt: userPrompt,
+        promptMetrics,
         context,
       });
     }

packages/adapters/pi-local/src/ui/build-config.ts

@@ -48,6 +48,7 @@ export function buildPiLocalConfig(v: CreateConfigValues): Record<string, unknow
   if (v.cwd) ac.cwd = v.cwd;
   if (v.instructionsFilePath) ac.instructionsFilePath = v.instructionsFilePath;
   if (v.promptTemplate) ac.promptTemplate = v.promptTemplate;
+  if (v.bootstrapPrompt) ac.bootstrapPromptTemplate = v.bootstrapPrompt;
   if (v.model) ac.model = v.model;
   if (v.thinkingEffort) ac.thinking = v.thinkingEffort;
   

packages/db/src/migrations/0028_harsh_goliath.sql

@@ -0,0 +1,54 @@
+CREATE TABLE "document_revisions" (
+	"id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+	"company_id" uuid NOT NULL,
+	"document_id" uuid NOT NULL,
+	"revision_number" integer NOT NULL,
+	"body" text NOT NULL,
+	"change_summary" text,
+	"created_by_agent_id" uuid,
+	"created_by_user_id" text,
+	"created_at" timestamp with time zone DEFAULT now() NOT NULL
+);
+--> statement-breakpoint
+CREATE TABLE "documents" (
+	"id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+	"company_id" uuid NOT NULL,
+	"title" text,
+	"format" text DEFAULT 'markdown' NOT NULL,
+	"latest_body" text NOT NULL,
+	"latest_revision_id" uuid,
+	"latest_revision_number" integer DEFAULT 1 NOT NULL,
+	"created_by_agent_id" uuid,
+	"created_by_user_id" text,
+	"updated_by_agent_id" uuid,
+	"updated_by_user_id" text,
+	"created_at" timestamp with time zone DEFAULT now() NOT NULL,
+	"updated_at" timestamp with time zone DEFAULT now() NOT NULL
+);
+--> statement-breakpoint
+CREATE TABLE "issue_documents" (
+	"id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+	"company_id" uuid NOT NULL,
+	"issue_id" uuid NOT NULL,
+	"document_id" uuid NOT NULL,
+	"key" text NOT NULL,
+	"created_at" timestamp with time zone DEFAULT now() NOT NULL,
+	"updated_at" timestamp with time zone DEFAULT now() NOT NULL
+);
+--> statement-breakpoint
+ALTER TABLE "document_revisions" ADD CONSTRAINT "document_revisions_company_id_companies_id_fk" FOREIGN KEY ("company_id") REFERENCES "public"."companies"("id") ON DELETE no action ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "document_revisions" ADD CONSTRAINT "document_revisions_document_id_documents_id_fk" FOREIGN KEY ("document_id") REFERENCES "public"."documents"("id") ON DELETE cascade ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "document_revisions" ADD CONSTRAINT "document_revisions_created_by_agent_id_agents_id_fk" FOREIGN KEY ("created_by_agent_id") REFERENCES "public"."agents"("id") ON DELETE set null ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "documents" ADD CONSTRAINT "documents_company_id_companies_id_fk" FOREIGN KEY ("company_id") REFERENCES "public"."companies"("id") ON DELETE no action ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "documents" ADD CONSTRAINT "documents_created_by_agent_id_agents_id_fk" FOREIGN KEY ("created_by_agent_id") REFERENCES "public"."agents"("id") ON DELETE set null ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "documents" ADD CONSTRAINT "documents_updated_by_agent_id_agents_id_fk" FOREIGN KEY ("updated_by_agent_id") REFERENCES "public"."agents"("id") ON DELETE set null ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "issue_documents" ADD CONSTRAINT "issue_documents_company_id_companies_id_fk" FOREIGN KEY ("company_id") REFERENCES "public"."companies"("id") ON DELETE no action ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "issue_documents" ADD CONSTRAINT "issue_documents_issue_id_issues_id_fk" FOREIGN KEY ("issue_id") REFERENCES "public"."issues"("id") ON DELETE cascade ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "issue_documents" ADD CONSTRAINT "issue_documents_document_id_documents_id_fk" FOREIGN KEY ("document_id") REFERENCES "public"."documents"("id") ON DELETE cascade ON UPDATE no action;--> statement-breakpoint
+CREATE UNIQUE INDEX "document_revisions_document_revision_uq" ON "document_revisions" USING btree ("document_id","revision_number");--> statement-breakpoint
+CREATE INDEX "document_revisions_company_document_created_idx" ON "document_revisions" USING btree ("company_id","document_id","created_at");--> statement-breakpoint
+CREATE INDEX "documents_company_updated_idx" ON "documents" USING btree ("company_id","updated_at");--> statement-breakpoint
+CREATE INDEX "documents_company_created_idx" ON "documents" USING btree ("company_id","created_at");--> statement-breakpoint
+CREATE UNIQUE INDEX "issue_documents_company_issue_key_uq" ON "issue_documents" USING btree ("company_id","issue_id","key");--> statement-breakpoint
+CREATE UNIQUE INDEX "issue_documents_document_uq" ON "issue_documents" USING btree ("document_id");--> statement-breakpoint
+CREATE INDEX "issue_documents_company_issue_updated_idx" ON "issue_documents" USING btree ("company_id","issue_id","updated_at");

packages/db/src/migrations/meta/_journal.json

@@ -201,8 +201,15 @@
     {
       "idx": 28,
       "version": "7",
+      "when": 1773432085646,
+      "tag": "0028_harsh_goliath",
+      "breakpoints": true
+    },
+    {
+      "idx": 29,
+      "version": "7",
       "when": 1773417600000,
-      "tag": "0028_plugin_tables",
+      "tag": "0029_plugin_tables",
       "breakpoints": true
     }
   ]

packages/db/src/schema/document_revisions.ts

@@ -0,0 +1,30 @@
+import { pgTable, uuid, text, integer, timestamp, index, uniqueIndex } from "drizzle-orm/pg-core";
+import { companies } from "./companies.js";
+import { agents } from "./agents.js";
+import { documents } from "./documents.js";
+
+export const documentRevisions = pgTable(
+  "document_revisions",
+  {
+    id: uuid("id").primaryKey().defaultRandom(),
+    companyId: uuid("company_id").notNull().references(() => companies.id),
+    documentId: uuid("document_id").notNull().references(() => documents.id, { onDelete: "cascade" }),
+    revisionNumber: integer("revision_number").notNull(),
+    body: text("body").notNull(),
+    changeSummary: text("change_summary"),
+    createdByAgentId: uuid("created_by_agent_id").references(() => agents.id, { onDelete: "set null" }),
+    createdByUserId: text("created_by_user_id"),
+    createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
+  },
+  (table) => ({
+    documentRevisionUq: uniqueIndex("document_revisions_document_revision_uq").on(
+      table.documentId,
+      table.revisionNumber,
+    ),
+    companyDocumentCreatedIdx: index("document_revisions_company_document_created_idx").on(
+      table.companyId,
+      table.documentId,
+      table.createdAt,
+    ),
+  }),
+);

packages/db/src/schema/documents.ts

@@ -0,0 +1,26 @@
+import { pgTable, uuid, text, integer, timestamp, index } from "drizzle-orm/pg-core";
+import { companies } from "./companies.js";
+import { agents } from "./agents.js";
+
+export const documents = pgTable(
+  "documents",
+  {
+    id: uuid("id").primaryKey().defaultRandom(),
+    companyId: uuid("company_id").notNull().references(() => companies.id),
+    title: text("title"),
+    format: text("format").notNull().default("markdown"),
+    latestBody: text("latest_body").notNull(),
+    latestRevisionId: uuid("latest_revision_id"),
+    latestRevisionNumber: integer("latest_revision_number").notNull().default(1),
+    createdByAgentId: uuid("created_by_agent_id").references(() => agents.id, { onDelete: "set null" }),
+    createdByUserId: text("created_by_user_id"),
+    updatedByAgentId: uuid("updated_by_agent_id").references(() => agents.id, { onDelete: "set null" }),
+    updatedByUserId: text("updated_by_user_id"),
+    createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
+    updatedAt: timestamp("updated_at", { withTimezone: true }).notNull().defaultNow(),
+  },
+  (table) => ({
+    companyUpdatedIdx: index("documents_company_updated_idx").on(table.companyId, table.updatedAt),
+    companyCreatedIdx: index("documents_company_created_idx").on(table.companyId, table.createdAt),
+  }),
+);

packages/db/src/schema/index.ts

@@ -24,6 +24,9 @@ export { issueComments } from "./issue_comments.js";
 export { issueReadStates } from "./issue_read_states.js";
 export { assets } from "./assets.js";
 export { issueAttachments } from "./issue_attachments.js";
+export { documents } from "./documents.js";
+export { documentRevisions } from "./document_revisions.js";
+export { issueDocuments } from "./issue_documents.js";
 export { heartbeatRuns } from "./heartbeat_runs.js";
 export { heartbeatRunEvents } from "./heartbeat_run_events.js";
 export { costEvents } from "./cost_events.js";

packages/db/src/schema/issue_documents.ts

@@ -0,0 +1,30 @@
+import { pgTable, uuid, text, timestamp, index, uniqueIndex } from "drizzle-orm/pg-core";
+import { companies } from "./companies.js";
+import { issues } from "./issues.js";
+import { documents } from "./documents.js";
+
+export const issueDocuments = pgTable(
+  "issue_documents",
+  {
+    id: uuid("id").primaryKey().defaultRandom(),
+    companyId: uuid("company_id").notNull().references(() => companies.id),
+    issueId: uuid("issue_id").notNull().references(() => issues.id, { onDelete: "cascade" }),
+    documentId: uuid("document_id").notNull().references(() => documents.id, { onDelete: "cascade" }),
+    key: text("key").notNull(),
+    createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
+    updatedAt: timestamp("updated_at", { withTimezone: true }).notNull().defaultNow(),
+  },
+  (table) => ({
+    companyIssueKeyUq: uniqueIndex("issue_documents_company_issue_key_uq").on(
+      table.companyId,
+      table.issueId,
+      table.key,
+    ),
+    documentUq: uniqueIndex("issue_documents_document_uq").on(table.documentId),
+    companyIssueUpdatedIdx: index("issue_documents_company_issue_updated_idx").on(
+      table.companyId,
+      table.issueId,
+      table.updatedAt,
+    ),
+  }),
+);

packages/shared/src/index.ts

@@ -119,6 +119,11 @@ export type {
   Issue,
   IssueAssigneeAdapterOverrides,
   IssueComment,
+  IssueDocument,
+  IssueDocumentSummary,
+  DocumentRevision,
+  DocumentFormat,
+  LegacyPlanDocument,
   IssueAttachment,
   IssueLabel,
   Goal,
@@ -225,6 +230,9 @@ export {
   addIssueCommentSchema,
   linkIssueApprovalSchema,
   createIssueAttachmentMetadataSchema,
+  issueDocumentFormatSchema,
+  issueDocumentKeySchema,
+  upsertIssueDocumentSchema,
   type CreateIssue,
   type CreateIssueLabel,
   type UpdateIssue,
@@ -232,6 +240,8 @@ export {
   type AddIssueComment,
   type LinkIssueApproval,
   type CreateIssueAttachmentMetadata,
+  type IssueDocumentFormat,
+  type UpsertIssueDocument,
   createGoalSchema,
   updateGoalSchema,
   type CreateGoal,

packages/shared/src/types/index.ts

@@ -23,6 +23,11 @@ export type {
   Issue,
   IssueAssigneeAdapterOverrides,
   IssueComment,
+  IssueDocument,
+  IssueDocumentSummary,
+  DocumentRevision,
+  DocumentFormat,
+  LegacyPlanDocument,
   IssueAncestor,
   IssueAncestorProject,
   IssueAncestorGoal,

packages/shared/src/types/issue.ts

@@ -50,6 +50,49 @@ export interface IssueAssigneeAdapterOverrides {
   useProjectWorkspace?: boolean;
 }
 
+export type DocumentFormat = "markdown";
+
+export interface IssueDocumentSummary {
+  id: string;
+  companyId: string;
+  issueId: string;
+  key: string;
+  title: string | null;
+  format: DocumentFormat;
+  latestRevisionId: string | null;
+  latestRevisionNumber: number;
+  createdByAgentId: string | null;
+  createdByUserId: string | null;
+  updatedByAgentId: string | null;
+  updatedByUserId: string | null;
+  createdAt: Date;
+  updatedAt: Date;
+}
+
+export interface IssueDocument extends IssueDocumentSummary {
+  body: string;
+}
+
+export interface DocumentRevision {
+  id: string;
+  companyId: string;
+  documentId: string;
+  issueId: string;
+  key: string;
+  revisionNumber: number;
+  body: string;
+  changeSummary: string | null;
+  createdByAgentId: string | null;
+  createdByUserId: string | null;
+  createdAt: Date;
+}
+
+export interface LegacyPlanDocument {
+  key: "plan";
+  body: string;
+  source: "issue_description";
+}
+
 export interface Issue {
   id: string;
   companyId: string;
@@ -81,6 +124,9 @@ export interface Issue {
   hiddenAt: Date | null;
   labelIds?: string[];
   labels?: IssueLabel[];
+  planDocument?: IssueDocument | null;
+  documentSummaries?: IssueDocumentSummary[];
+  legacyPlanDocument?: LegacyPlanDocument | null;
   project?: Project | null;
   goal?: Goal | null;
   mentionedProjects?: Project[];

packages/shared/src/validators/agent.ts

@@ -78,6 +78,10 @@ export const wakeAgentSchema = z.object({
   reason: z.string().optional().nullable(),
   payload: z.record(z.unknown()).optional().nullable(),
   idempotencyKey: z.string().optional().nullable(),
+  forceFreshSession: z.preprocess(
+    (value) => (value === null ? undefined : value),
+    z.boolean().optional().default(false),
+  ),
 });
 
 export type WakeAgent = z.infer<typeof wakeAgentSchema>;

packages/shared/src/validators/index.ts

@@ -66,6 +66,9 @@ export {
   addIssueCommentSchema,
   linkIssueApprovalSchema,
   createIssueAttachmentMetadataSchema,
+  issueDocumentFormatSchema,
+  issueDocumentKeySchema,
+  upsertIssueDocumentSchema,
   type CreateIssue,
   type CreateIssueLabel,
   type UpdateIssue,
@@ -74,6 +77,8 @@ export {
   type AddIssueComment,
   type LinkIssueApproval,
   type CreateIssueAttachmentMetadata,
+  type IssueDocumentFormat,
+  type UpsertIssueDocument,
 } from "./issue.js";
 
 export {

packages/shared/src/validators/issue.ts

@@ -87,3 +87,25 @@ export const createIssueAttachmentMetadataSchema = z.object({
 });
 
 export type CreateIssueAttachmentMetadata = z.infer<typeof createIssueAttachmentMetadataSchema>;
+
+export const ISSUE_DOCUMENT_FORMATS = ["markdown"] as const;
+
+export const issueDocumentFormatSchema = z.enum(ISSUE_DOCUMENT_FORMATS);
+
+export const issueDocumentKeySchema = z
+  .string()
+  .trim()
+  .min(1)
+  .max(64)
+  .regex(/^[a-z0-9][a-z0-9_-]*$/, "Document key must be lowercase letters, numbers, _ or -");
+
+export const upsertIssueDocumentSchema = z.object({
+  title: z.string().trim().max(200).nullable().optional(),
+  format: issueDocumentFormatSchema,
+  body: z.string().max(524288),
+  changeSummary: z.string().trim().max(500).nullable().optional(),
+  baseRevisionId: z.string().uuid().nullable().optional(),
+});
+
+export type IssueDocumentFormat = z.infer<typeof issueDocumentFormatSchema>;
+export type UpsertIssueDocument = z.infer<typeof upsertIssueDocumentSchema>;

report/2026-03-13-08-46-token-optimization-implementation.md

@@ -0,0 +1,48 @@
+# Token Optimization Implementation Report
+
+Implemented the token-optimization plan across heartbeat orchestration, issue context APIs, adapter prompt construction, skill exposure, and agent configuration UX.
+
+The main behavior changes are:
+
+- Heartbeat telemetry now normalizes sessioned local adapter usage as per-run deltas instead of blindly trusting cumulative session totals.
+- Timer and manual wakes now preserve task sessions by default; fresh sessions are forced only for explicit `forceFreshSession` wakes or new issue assignment wakes.
+- Heartbeat session rotation is now policy-driven in the control plane, with a handoff note injected when a session is compacted and restarted.
+- Paperclip issue context now has incremental APIs: `GET /api/agents/me/inbox-lite`, `GET /api/issues/:id/heartbeat-context`, and comment delta queries via `GET /api/issues/:id/comments?after=...&order=asc`.
+- The `paperclip` skill now teaches agents to use those compact/incremental APIs first, while keeping full-thread fetches as a cold-start fallback.
+- All local adapters now separate first-session bootstrap prompts from per-heartbeat prompt templates, and emit prompt size metrics in invocation metadata.
+- Adapter create flows now persist `bootstrapPromptTemplate` correctly.
+- The agent config UI now explains the difference between bootstrap prompts and heartbeat prompts and warns about prompt churn.
+- Runtime skill defaults now include `paperclip`, `para-memory-files`, and `paperclip-create-agent`. `create-agent-adapter` was moved to `.agents/skills/create-agent-adapter`.
+
+Important follow-up finding from real-run review:
+
+- `codex_local` currently injects Paperclip skills into the shared Codex skills home (`$CODEX_HOME/skills` or `~/.codex/skills`) rather than mounting a worktree-local skill directory.
+- If a Paperclip-owned skill symlink already points at another live checkout, the adapter currently skips it instead of repointing it.
+- In practice, this means a worktree can contain newer `skills/paperclip/SKILL.md` guidance while Codex still follows an older checkout's skill content.
+- That likely explains why PAP-507 still showed full issue/comment reload behavior even though the incremental context work was already implemented in this branch.
+- This should be treated as a separate follow-up item for `codex_local` skill isolation or symlink repair.
+
+Files with the most important implementation work:
+
+- `server/src/services/heartbeat.ts`
+- `server/src/services/issues.ts`
+- `server/src/routes/issues.ts`
+- `server/src/routes/agents.ts`
+- `server/src/routes/access.ts`
+- `skills/paperclip/SKILL.md`
+- `packages/adapters/*/src/server/execute.ts`
+- `packages/adapters/*/src/ui/build-config.ts`
+- `ui/src/components/AgentConfigForm.tsx`
+
+Verification completed successfully:
+
+- `pnpm -r typecheck`
+- `pnpm test:run`
+- `pnpm build`
+
+While verifying, I also fixed two existing embedded-postgres typing mismatches so repo-wide `typecheck` and `build` pass again:
+
+- `packages/db/src/migration-runtime.ts`
+- `cli/src/commands/worktree.ts`
+
+Next useful follow-up is measuring the before/after effect in real runs now that telemetry is less misleading and prompt/session reuse behavior is consistent across adapters.

server/src/__tests__/codex-local-execute.test.ts

@@ -0,0 +1,208 @@
+import { describe, expect, it } from "vitest";
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+import { execute } from "@paperclipai/adapter-codex-local/server";
+
+async function writeFakeCodexCommand(commandPath: string): Promise<void> {
+  const script = `#!/usr/bin/env node
+const fs = require("node:fs");
+
+const capturePath = process.env.PAPERCLIP_TEST_CAPTURE_PATH;
+const payload = {
+  argv: process.argv.slice(2),
+  prompt: fs.readFileSync(0, "utf8"),
+  codexHome: process.env.CODEX_HOME || null,
+  paperclipEnvKeys: Object.keys(process.env)
+    .filter((key) => key.startsWith("PAPERCLIP_"))
+    .sort(),
+};
+if (capturePath) {
+  fs.writeFileSync(capturePath, JSON.stringify(payload), "utf8");
+}
+console.log(JSON.stringify({ type: "thread.started", thread_id: "codex-session-1" }));
+console.log(JSON.stringify({ type: "item.completed", item: { type: "agent_message", text: "hello" } }));
+console.log(JSON.stringify({ type: "turn.completed", usage: { input_tokens: 1, cached_input_tokens: 0, output_tokens: 1 } }));
+`;
+  await fs.writeFile(commandPath, script, "utf8");
+  await fs.chmod(commandPath, 0o755);
+}
+
+type CapturePayload = {
+  argv: string[];
+  prompt: string;
+  codexHome: string | null;
+  paperclipEnvKeys: string[];
+};
+
+describe("codex execute", () => {
+  it("uses a worktree-isolated CODEX_HOME while preserving shared auth and config", async () => {
+    const root = await fs.mkdtemp(path.join(os.tmpdir(), "paperclip-codex-execute-"));
+    const workspace = path.join(root, "workspace");
+    const commandPath = path.join(root, "codex");
+    const capturePath = path.join(root, "capture.json");
+    const sharedCodexHome = path.join(root, "shared-codex-home");
+    const paperclipHome = path.join(root, "paperclip-home");
+    const isolatedCodexHome = path.join(paperclipHome, "instances", "worktree-1", "codex-home");
+    await fs.mkdir(workspace, { recursive: true });
+    await fs.mkdir(sharedCodexHome, { recursive: true });
+    await fs.writeFile(path.join(sharedCodexHome, "auth.json"), '{"token":"shared"}\n', "utf8");
+    await fs.writeFile(path.join(sharedCodexHome, "config.toml"), 'model = "codex-mini-latest"\n', "utf8");
+    await writeFakeCodexCommand(commandPath);
+
+    const previousHome = process.env.HOME;
+    const previousPaperclipHome = process.env.PAPERCLIP_HOME;
+    const previousPaperclipInstanceId = process.env.PAPERCLIP_INSTANCE_ID;
+    const previousPaperclipInWorktree = process.env.PAPERCLIP_IN_WORKTREE;
+    const previousCodexHome = process.env.CODEX_HOME;
+    process.env.HOME = root;
+    process.env.PAPERCLIP_HOME = paperclipHome;
+    process.env.PAPERCLIP_INSTANCE_ID = "worktree-1";
+    process.env.PAPERCLIP_IN_WORKTREE = "true";
+    process.env.CODEX_HOME = sharedCodexHome;
+
+    try {
+      const result = await execute({
+        runId: "run-1",
+        agent: {
+          id: "agent-1",
+          companyId: "company-1",
+          name: "Codex Coder",
+          adapterType: "codex_local",
+          adapterConfig: {},
+        },
+        runtime: {
+          sessionId: null,
+          sessionParams: null,
+          sessionDisplayId: null,
+          taskKey: null,
+        },
+        config: {
+          command: commandPath,
+          cwd: workspace,
+          env: {
+            PAPERCLIP_TEST_CAPTURE_PATH: capturePath,
+          },
+          promptTemplate: "Follow the paperclip heartbeat.",
+        },
+        context: {},
+        authToken: "run-jwt-token",
+        onLog: async () => {},
+      });
+
+      expect(result.exitCode).toBe(0);
+      expect(result.errorMessage).toBeNull();
+
+      const capture = JSON.parse(await fs.readFile(capturePath, "utf8")) as CapturePayload;
+      expect(capture.codexHome).toBe(isolatedCodexHome);
+      expect(capture.argv).toEqual(expect.arrayContaining(["exec", "--json", "-"]));
+      expect(capture.prompt).toContain("Follow the paperclip heartbeat.");
+      expect(capture.paperclipEnvKeys).toEqual(
+        expect.arrayContaining([
+          "PAPERCLIP_AGENT_ID",
+          "PAPERCLIP_API_KEY",
+          "PAPERCLIP_API_URL",
+          "PAPERCLIP_COMPANY_ID",
+          "PAPERCLIP_RUN_ID",
+        ]),
+      );
+
+      const isolatedAuth = path.join(isolatedCodexHome, "auth.json");
+      const isolatedConfig = path.join(isolatedCodexHome, "config.toml");
+      const isolatedSkill = path.join(isolatedCodexHome, "skills", "paperclip");
+
+      expect((await fs.lstat(isolatedAuth)).isSymbolicLink()).toBe(true);
+      expect(await fs.realpath(isolatedAuth)).toBe(await fs.realpath(path.join(sharedCodexHome, "auth.json")));
+      expect((await fs.lstat(isolatedConfig)).isFile()).toBe(true);
+      expect(await fs.readFile(isolatedConfig, "utf8")).toBe('model = "codex-mini-latest"\n');
+      expect((await fs.lstat(isolatedSkill)).isSymbolicLink()).toBe(true);
+    } finally {
+      if (previousHome === undefined) delete process.env.HOME;
+      else process.env.HOME = previousHome;
+      if (previousPaperclipHome === undefined) delete process.env.PAPERCLIP_HOME;
+      else process.env.PAPERCLIP_HOME = previousPaperclipHome;
+      if (previousPaperclipInstanceId === undefined) delete process.env.PAPERCLIP_INSTANCE_ID;
+      else process.env.PAPERCLIP_INSTANCE_ID = previousPaperclipInstanceId;
+      if (previousPaperclipInWorktree === undefined) delete process.env.PAPERCLIP_IN_WORKTREE;
+      else process.env.PAPERCLIP_IN_WORKTREE = previousPaperclipInWorktree;
+      if (previousCodexHome === undefined) delete process.env.CODEX_HOME;
+      else process.env.CODEX_HOME = previousCodexHome;
+      await fs.rm(root, { recursive: true, force: true });
+    }
+  });
+
+  it("respects an explicit CODEX_HOME config override even in worktree mode", async () => {
+    const root = await fs.mkdtemp(path.join(os.tmpdir(), "paperclip-codex-execute-explicit-"));
+    const workspace = path.join(root, "workspace");
+    const commandPath = path.join(root, "codex");
+    const capturePath = path.join(root, "capture.json");
+    const sharedCodexHome = path.join(root, "shared-codex-home");
+    const explicitCodexHome = path.join(root, "explicit-codex-home");
+    const paperclipHome = path.join(root, "paperclip-home");
+    await fs.mkdir(workspace, { recursive: true });
+    await fs.mkdir(sharedCodexHome, { recursive: true });
+    await fs.writeFile(path.join(sharedCodexHome, "auth.json"), '{"token":"shared"}\n', "utf8");
+    await writeFakeCodexCommand(commandPath);
+
+    const previousHome = process.env.HOME;
+    const previousPaperclipHome = process.env.PAPERCLIP_HOME;
+    const previousPaperclipInstanceId = process.env.PAPERCLIP_INSTANCE_ID;
+    const previousPaperclipInWorktree = process.env.PAPERCLIP_IN_WORKTREE;
+    const previousCodexHome = process.env.CODEX_HOME;
+    process.env.HOME = root;
+    process.env.PAPERCLIP_HOME = paperclipHome;
+    process.env.PAPERCLIP_INSTANCE_ID = "worktree-1";
+    process.env.PAPERCLIP_IN_WORKTREE = "true";
+    process.env.CODEX_HOME = sharedCodexHome;
+
+    try {
+      const result = await execute({
+        runId: "run-2",
+        agent: {
+          id: "agent-1",
+          companyId: "company-1",
+          name: "Codex Coder",
+          adapterType: "codex_local",
+          adapterConfig: {},
+        },
+        runtime: {
+          sessionId: null,
+          sessionParams: null,
+          sessionDisplayId: null,
+          taskKey: null,
+        },
+        config: {
+          command: commandPath,
+          cwd: workspace,
+          env: {
+            PAPERCLIP_TEST_CAPTURE_PATH: capturePath,
+            CODEX_HOME: explicitCodexHome,
+          },
+          promptTemplate: "Follow the paperclip heartbeat.",
+        },
+        context: {},
+        authToken: "run-jwt-token",
+        onLog: async () => {},
+      });
+
+      expect(result.exitCode).toBe(0);
+      expect(result.errorMessage).toBeNull();
+
+      const capture = JSON.parse(await fs.readFile(capturePath, "utf8")) as CapturePayload;
+      expect(capture.codexHome).toBe(explicitCodexHome);
+      await expect(fs.lstat(path.join(paperclipHome, "instances", "worktree-1", "codex-home"))).rejects.toThrow();
+    } finally {
+      if (previousHome === undefined) delete process.env.HOME;
+      else process.env.HOME = previousHome;
+      if (previousPaperclipHome === undefined) delete process.env.PAPERCLIP_HOME;
+      else process.env.PAPERCLIP_HOME = previousPaperclipHome;
+      if (previousPaperclipInstanceId === undefined) delete process.env.PAPERCLIP_INSTANCE_ID;
+      else process.env.PAPERCLIP_INSTANCE_ID = previousPaperclipInstanceId;
+      if (previousPaperclipInWorktree === undefined) delete process.env.PAPERCLIP_IN_WORKTREE;
+      else process.env.PAPERCLIP_IN_WORKTREE = previousPaperclipInWorktree;
+      if (previousCodexHome === undefined) delete process.env.CODEX_HOME;
+      else process.env.CODEX_HOME = previousCodexHome;
+      await fs.rm(root, { recursive: true, force: true });
+    }
+  });
+});

server/src/__tests__/codex-local-skill-injection.test.ts

@@ -0,0 +1,91 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+import { afterEach, describe, expect, it } from "vitest";
+import { ensureCodexSkillsInjected } from "@paperclipai/adapter-codex-local/server";
+
+async function makeTempDir(prefix: string): Promise<string> {
+  return fs.mkdtemp(path.join(os.tmpdir(), prefix));
+}
+
+async function createPaperclipRepoSkill(root: string, skillName: string) {
+  await fs.mkdir(path.join(root, "server"), { recursive: true });
+  await fs.mkdir(path.join(root, "packages", "adapter-utils"), { recursive: true });
+  await fs.mkdir(path.join(root, "skills", skillName), { recursive: true });
+  await fs.writeFile(path.join(root, "pnpm-workspace.yaml"), "packages:\n  - packages/*\n", "utf8");
+  await fs.writeFile(path.join(root, "package.json"), '{"name":"paperclip"}\n', "utf8");
+  await fs.writeFile(
+    path.join(root, "skills", skillName, "SKILL.md"),
+    `---\nname: ${skillName}\n---\n`,
+    "utf8",
+  );
+}
+
+async function createCustomSkill(root: string, skillName: string) {
+  await fs.mkdir(path.join(root, "custom", skillName), { recursive: true });
+  await fs.writeFile(
+    path.join(root, "custom", skillName, "SKILL.md"),
+    `---\nname: ${skillName}\n---\n`,
+    "utf8",
+  );
+}
+
+describe("codex local adapter skill injection", () => {
+  const cleanupDirs = new Set<string>();
+
+  afterEach(async () => {
+    await Promise.all(Array.from(cleanupDirs).map((dir) => fs.rm(dir, { recursive: true, force: true })));
+    cleanupDirs.clear();
+  });
+
+  it("repairs a Codex Paperclip skill symlink that still points at another live checkout", async () => {
+    const currentRepo = await makeTempDir("paperclip-codex-current-");
+    const oldRepo = await makeTempDir("paperclip-codex-old-");
+    const skillsHome = await makeTempDir("paperclip-codex-home-");
+    cleanupDirs.add(currentRepo);
+    cleanupDirs.add(oldRepo);
+    cleanupDirs.add(skillsHome);
+
+    await createPaperclipRepoSkill(currentRepo, "paperclip");
+    await createPaperclipRepoSkill(oldRepo, "paperclip");
+    await fs.symlink(path.join(oldRepo, "skills", "paperclip"), path.join(skillsHome, "paperclip"));
+
+    const logs: string[] = [];
+    await ensureCodexSkillsInjected(
+      async (_stream, chunk) => {
+        logs.push(chunk);
+      },
+      {
+        skillsHome,
+        skillsEntries: [{ name: "paperclip", source: path.join(currentRepo, "skills", "paperclip") }],
+      },
+    );
+
+    expect(await fs.realpath(path.join(skillsHome, "paperclip"))).toBe(
+      await fs.realpath(path.join(currentRepo, "skills", "paperclip")),
+    );
+    expect(logs.some((line) => line.includes('Repaired Codex skill "paperclip"'))).toBe(true);
+  });
+
+  it("preserves a custom Codex skill symlink outside Paperclip repo checkouts", async () => {
+    const currentRepo = await makeTempDir("paperclip-codex-current-");
+    const customRoot = await makeTempDir("paperclip-codex-custom-");
+    const skillsHome = await makeTempDir("paperclip-codex-home-");
+    cleanupDirs.add(currentRepo);
+    cleanupDirs.add(customRoot);
+    cleanupDirs.add(skillsHome);
+
+    await createPaperclipRepoSkill(currentRepo, "paperclip");
+    await createCustomSkill(customRoot, "paperclip");
+    await fs.symlink(path.join(customRoot, "custom", "paperclip"), path.join(skillsHome, "paperclip"));
+
+    await ensureCodexSkillsInjected(async () => {}, {
+      skillsHome,
+      skillsEntries: [{ name: "paperclip", source: path.join(currentRepo, "skills", "paperclip") }],
+    });
+
+    expect(await fs.realpath(path.join(skillsHome, "paperclip"))).toBe(
+      await fs.realpath(path.join(customRoot, "custom", "paperclip")),
+    );
+  });
+});

server/src/__tests__/documents.test.ts

@@ -0,0 +1,29 @@
+import { describe, expect, it } from "vitest";
+import { extractLegacyPlanBody } from "../services/documents.js";
+
+describe("extractLegacyPlanBody", () => {
+  it("returns null when no plan block exists", () => {
+    expect(extractLegacyPlanBody("hello world")).toBeNull();
+  });
+
+  it("extracts plan body from legacy issue descriptions", () => {
+    expect(
+      extractLegacyPlanBody(`
+intro
+
+<plan>
+
+# Plan
+
+- one
+- two
+
+</plan>
+      `),
+    ).toBe("# Plan\n\n- one\n- two");
+  });
+
+  it("ignores empty plan blocks", () => {
+    expect(extractLegacyPlanBody("<plan>   </plan>")).toBeNull();
+  });
+});

server/src/__tests__/heartbeat-workspace-session.test.ts

@@ -93,16 +93,26 @@ describe("shouldResetTaskSessionForWake", () => {
     expect(shouldResetTaskSessionForWake({ wakeReason: "issue_assigned" })).toBe(true);
   });
 
-  it("resets session context on timer heartbeats", () => {
-    expect(shouldResetTaskSessionForWake({ wakeSource: "timer" })).toBe(true);
+  it("preserves session context on timer heartbeats", () => {
+    expect(shouldResetTaskSessionForWake({ wakeSource: "timer" })).toBe(false);
   });
 
-  it("resets session context on manual on-demand invokes", () => {
+  it("preserves session context on manual on-demand invokes by default", () => {
     expect(
       shouldResetTaskSessionForWake({
         wakeSource: "on_demand",
         wakeTriggerDetail: "manual",
       }),
+    ).toBe(false);
+  });
+
+  it("resets session context when a fresh session is explicitly requested", () => {
+    expect(
+      shouldResetTaskSessionForWake({
+        wakeSource: "on_demand",
+        wakeTriggerDetail: "manual",
+        forceFreshSession: true,
+      }),
     ).toBe(true);
   });
 

server/src/attachment-types.ts

@@ -21,6 +21,12 @@ export const DEFAULT_ALLOWED_TYPES: readonly string[] = [
   "image/jpg",
   "image/webp",
   "image/gif",
+  "application/pdf",
+  "text/markdown",
+  "text/plain",
+  "application/json",
+  "text/csv",
+  "text/html",
 ];
 
 /**

server/src/routes/access.ts

@@ -97,7 +97,11 @@ function requestBaseUrl(req: Request) {
 
 function readSkillMarkdown(skillName: string): string | null {
   const normalized = skillName.trim().toLowerCase();
-  if (normalized !== "paperclip" && normalized !== "paperclip-create-agent")
+  if (
+    normalized !== "paperclip" &&
+    normalized !== "paperclip-create-agent" &&
+    normalized !== "para-memory-files"
+  )
     return null;
   const moduleDir = path.dirname(fileURLToPath(import.meta.url));
   const candidates = [
@@ -1610,6 +1614,10 @@ export function accessRoutes(
     res.json({
       skills: [
         { name: "paperclip", path: "/api/skills/paperclip" },
+        {
+          name: "para-memory-files",
+          path: "/api/skills/para-memory-files"
+        },
         {
           name: "paperclip-create-agent",
           path: "/api/skills/paperclip-create-agent"

server/src/routes/agents.ts

@@ -575,6 +575,34 @@ export function agentRoutes(db: Db) {
     res.json({ ...agent, chainOfCommand });
   });
 
+  router.get("/agents/me/inbox-lite", async (req, res) => {
+    if (req.actor.type !== "agent" || !req.actor.agentId || !req.actor.companyId) {
+      res.status(401).json({ error: "Agent authentication required" });
+      return;
+    }
+
+    const issuesSvc = issueService(db);
+    const rows = await issuesSvc.list(req.actor.companyId, {
+      assigneeAgentId: req.actor.agentId,
+      status: "todo,in_progress,blocked",
+    });
+
+    res.json(
+      rows.map((issue) => ({
+        id: issue.id,
+        identifier: issue.identifier,
+        title: issue.title,
+        status: issue.status,
+        priority: issue.priority,
+        projectId: issue.projectId,
+        goalId: issue.goalId,
+        parentId: issue.parentId,
+        updatedAt: issue.updatedAt,
+        activeRun: issue.activeRun,
+      })),
+    );
+  });
+
   router.get("/agents/:id", async (req, res) => {
     const id = req.params.id as string;
     const agent = await svc.getById(id);
@@ -1275,6 +1303,7 @@ export function agentRoutes(db: Db) {
       contextSnapshot: {
         triggeredBy: req.actor.type,
         actorId: req.actor.type === "agent" ? req.actor.agentId : req.actor.userId,
+        forceFreshSession: req.body.forceFreshSession === true,
       },
     });
 

server/src/routes/issues.ts

@@ -8,6 +8,8 @@ import {
   checkoutIssueSchema,
   createIssueSchema,
   linkIssueApprovalSchema,
+  issueDocumentKeySchema,
+  upsertIssueDocumentSchema,
   updateIssueSchema,
 } from "@paperclipai/shared";
 import type { StorageService } from "../storage/types.js";
@@ -19,6 +21,7 @@ import {
   heartbeatService,
   issueApprovalService,
   issueService,
+  documentService,
   logActivity,
   projectService,
 } from "../services/index.js";
@@ -28,6 +31,8 @@ import { assertCompanyAccess, getActorInfo } from "./authz.js";
 import { shouldWakeAssigneeOnCheckout } from "./issues-checkout-wakeup.js";
 import { isAllowedContentType, MAX_ATTACHMENT_BYTES } from "../attachment-types.js";
 
+const MAX_ISSUE_COMMENT_LIMIT = 500;
+
 export function issueRoutes(db: Db, storage: StorageService) {
   const router = Router();
   const svc = issueService(db);
@@ -37,6 +42,7 @@ export function issueRoutes(db: Db, storage: StorageService) {
   const projectsSvc = projectService(db);
   const goalsSvc = goalService(db);
   const issueApprovalsSvc = issueApprovalService(db);
+  const documentsSvc = documentService(db);
   const upload = multer({
     storage: multer.memoryStorage(),
     limits: { fileSize: MAX_ATTACHMENT_BYTES, files: 1 },
@@ -291,7 +297,7 @@ export function issueRoutes(db: Db, storage: StorageService) {
       return;
     }
     assertCompanyAccess(req, issue.companyId);
-    const [ancestors, project, goal, mentionedProjectIds] = await Promise.all([
+    const [ancestors, project, goal, mentionedProjectIds, documentPayload] = await Promise.all([
       svc.getAncestors(issue.id),
       issue.projectId ? projectsSvc.getById(issue.projectId) : null,
       issue.goalId
@@ -300,6 +306,7 @@ export function issueRoutes(db: Db, storage: StorageService) {
           ? goalsSvc.getDefaultCompanyGoal(issue.companyId)
           : null,
       svc.findMentionedProjectIds(issue.id),
+      documentsSvc.getIssueDocumentPayload(issue),
     ]);
     const mentionedProjects = mentionedProjectIds.length > 0
       ? await projectsSvc.listByIds(issue.companyId, mentionedProjectIds)
@@ -308,12 +315,226 @@ export function issueRoutes(db: Db, storage: StorageService) {
       ...issue,
       goalId: goal?.id ?? issue.goalId,
       ancestors,
+      ...documentPayload,
       project: project ?? null,
       goal: goal ?? null,
       mentionedProjects,
     });
   });
 
+  router.get("/issues/:id/heartbeat-context", async (req, res) => {
+    const id = req.params.id as string;
+    const issue = await svc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+
+    const wakeCommentId =
+      typeof req.query.wakeCommentId === "string" && req.query.wakeCommentId.trim().length > 0
+        ? req.query.wakeCommentId.trim()
+        : null;
+
+    const [ancestors, project, goal, commentCursor, wakeComment] = await Promise.all([
+      svc.getAncestors(issue.id),
+      issue.projectId ? projectsSvc.getById(issue.projectId) : null,
+      issue.goalId
+        ? goalsSvc.getById(issue.goalId)
+        : !issue.projectId
+          ? goalsSvc.getDefaultCompanyGoal(issue.companyId)
+          : null,
+      svc.getCommentCursor(issue.id),
+      wakeCommentId ? svc.getComment(wakeCommentId) : null,
+    ]);
+
+    res.json({
+      issue: {
+        id: issue.id,
+        identifier: issue.identifier,
+        title: issue.title,
+        description: issue.description,
+        status: issue.status,
+        priority: issue.priority,
+        projectId: issue.projectId,
+        goalId: goal?.id ?? issue.goalId,
+        parentId: issue.parentId,
+        assigneeAgentId: issue.assigneeAgentId,
+        assigneeUserId: issue.assigneeUserId,
+        updatedAt: issue.updatedAt,
+      },
+      ancestors: ancestors.map((ancestor) => ({
+        id: ancestor.id,
+        identifier: ancestor.identifier,
+        title: ancestor.title,
+        status: ancestor.status,
+        priority: ancestor.priority,
+      })),
+      project: project
+        ? {
+            id: project.id,
+            name: project.name,
+            status: project.status,
+            targetDate: project.targetDate,
+          }
+        : null,
+      goal: goal
+        ? {
+            id: goal.id,
+            title: goal.title,
+            status: goal.status,
+            level: goal.level,
+            parentId: goal.parentId,
+          }
+        : null,
+      commentCursor,
+      wakeComment:
+        wakeComment && wakeComment.issueId === issue.id
+          ? wakeComment
+          : null,
+    });
+  });
+
+  router.get("/issues/:id/documents", async (req, res) => {
+    const id = req.params.id as string;
+    const issue = await svc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+    const docs = await documentsSvc.listIssueDocuments(issue.id);
+    res.json(docs);
+  });
+
+  router.get("/issues/:id/documents/:key", async (req, res) => {
+    const id = req.params.id as string;
+    const issue = await svc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+    const keyParsed = issueDocumentKeySchema.safeParse(String(req.params.key ?? "").trim().toLowerCase());
+    if (!keyParsed.success) {
+      res.status(400).json({ error: "Invalid document key", details: keyParsed.error.issues });
+      return;
+    }
+    const doc = await documentsSvc.getIssueDocumentByKey(issue.id, keyParsed.data);
+    if (!doc) {
+      res.status(404).json({ error: "Document not found" });
+      return;
+    }
+    res.json(doc);
+  });
+
+  router.put("/issues/:id/documents/:key", validate(upsertIssueDocumentSchema), async (req, res) => {
+    const id = req.params.id as string;
+    const issue = await svc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+    const keyParsed = issueDocumentKeySchema.safeParse(String(req.params.key ?? "").trim().toLowerCase());
+    if (!keyParsed.success) {
+      res.status(400).json({ error: "Invalid document key", details: keyParsed.error.issues });
+      return;
+    }
+
+    const actor = getActorInfo(req);
+    const result = await documentsSvc.upsertIssueDocument({
+      issueId: issue.id,
+      key: keyParsed.data,
+      title: req.body.title ?? null,
+      format: req.body.format,
+      body: req.body.body,
+      changeSummary: req.body.changeSummary ?? null,
+      baseRevisionId: req.body.baseRevisionId ?? null,
+      createdByAgentId: actor.agentId ?? null,
+      createdByUserId: actor.actorType === "user" ? actor.actorId : null,
+    });
+    const doc = result.document;
+
+    await logActivity(db, {
+      companyId: issue.companyId,
+      actorType: actor.actorType,
+      actorId: actor.actorId,
+      agentId: actor.agentId,
+      runId: actor.runId,
+      action: result.created ? "issue.document_created" : "issue.document_updated",
+      entityType: "issue",
+      entityId: issue.id,
+      details: {
+        key: doc.key,
+        documentId: doc.id,
+        title: doc.title,
+        format: doc.format,
+        revisionNumber: doc.latestRevisionNumber,
+      },
+    });
+
+    res.status(result.created ? 201 : 200).json(doc);
+  });
+
+  router.get("/issues/:id/documents/:key/revisions", async (req, res) => {
+    const id = req.params.id as string;
+    const issue = await svc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+    const keyParsed = issueDocumentKeySchema.safeParse(String(req.params.key ?? "").trim().toLowerCase());
+    if (!keyParsed.success) {
+      res.status(400).json({ error: "Invalid document key", details: keyParsed.error.issues });
+      return;
+    }
+    const revisions = await documentsSvc.listIssueDocumentRevisions(issue.id, keyParsed.data);
+    res.json(revisions);
+  });
+
+  router.delete("/issues/:id/documents/:key", async (req, res) => {
+    const id = req.params.id as string;
+    const issue = await svc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+    if (req.actor.type !== "board") {
+      res.status(403).json({ error: "Board authentication required" });
+      return;
+    }
+    const keyParsed = issueDocumentKeySchema.safeParse(String(req.params.key ?? "").trim().toLowerCase());
+    if (!keyParsed.success) {
+      res.status(400).json({ error: "Invalid document key", details: keyParsed.error.issues });
+      return;
+    }
+    const removed = await documentsSvc.deleteIssueDocument(issue.id, keyParsed.data);
+    if (!removed) {
+      res.status(404).json({ error: "Document not found" });
+      return;
+    }
+    const actor = getActorInfo(req);
+    await logActivity(db, {
+      companyId: issue.companyId,
+      actorType: actor.actorType,
+      actorId: actor.actorId,
+      agentId: actor.agentId,
+      runId: actor.runId,
+      action: "issue.document_deleted",
+      entityType: "issue",
+      entityId: issue.id,
+      details: {
+        key: removed.key,
+        documentId: removed.id,
+        title: removed.title,
+      },
+    });
+    res.json({ ok: true });
+  });
+
   router.post("/issues/:id/read", async (req, res) => {
     const id = req.params.id as string;
     const issue = await svc.getById(id);
@@ -791,7 +1012,29 @@ export function issueRoutes(db: Db, storage: StorageService) {
       return;
     }
     assertCompanyAccess(req, issue.companyId);
-    const comments = await svc.listComments(id);
+    const afterCommentId =
+      typeof req.query.after === "string" && req.query.after.trim().length > 0
+        ? req.query.after.trim()
+        : typeof req.query.afterCommentId === "string" && req.query.afterCommentId.trim().length > 0
+          ? req.query.afterCommentId.trim()
+          : null;
+    const order =
+      typeof req.query.order === "string" && req.query.order.trim().toLowerCase() === "asc"
+        ? "asc"
+        : "desc";
+    const limitRaw =
+      typeof req.query.limit === "string" && req.query.limit.trim().length > 0
+        ? Number(req.query.limit)
+        : null;
+    const limit =
+      limitRaw && Number.isFinite(limitRaw) && limitRaw > 0
+        ? Math.min(Math.floor(limitRaw), MAX_ISSUE_COMMENT_LIMIT)
+        : null;
+    const comments = await svc.listComments(id, {
+      afterCommentId,
+      order,
+      limit,
+    });
     res.json(comments);
   });
 

server/src/services/documents.ts

@@ -0,0 +1,433 @@
+import { and, asc, desc, eq } from "drizzle-orm";
+import type { Db } from "@paperclipai/db";
+import { documentRevisions, documents, issueDocuments, issues } from "@paperclipai/db";
+import { issueDocumentKeySchema } from "@paperclipai/shared";
+import { conflict, notFound, unprocessable } from "../errors.js";
+
+function normalizeDocumentKey(key: string) {
+  const normalized = key.trim().toLowerCase();
+  const parsed = issueDocumentKeySchema.safeParse(normalized);
+  if (!parsed.success) {
+    throw unprocessable("Invalid document key", parsed.error.issues);
+  }
+  return parsed.data;
+}
+
+function isUniqueViolation(error: unknown): boolean {
+  return !!error && typeof error === "object" && "code" in error && (error as { code?: string }).code === "23505";
+}
+
+export function extractLegacyPlanBody(description: string | null | undefined) {
+  if (!description) return null;
+  const match = /<plan>\s*([\s\S]*?)\s*<\/plan>/i.exec(description);
+  if (!match) return null;
+  const body = match[1]?.trim();
+  return body ? body : null;
+}
+
+function mapIssueDocumentRow(
+  row: {
+    id: string;
+    companyId: string;
+    issueId: string;
+    key: string;
+    title: string | null;
+    format: string;
+    latestBody: string;
+    latestRevisionId: string | null;
+    latestRevisionNumber: number;
+    createdByAgentId: string | null;
+    createdByUserId: string | null;
+    updatedByAgentId: string | null;
+    updatedByUserId: string | null;
+    createdAt: Date;
+    updatedAt: Date;
+  },
+  includeBody: boolean,
+) {
+  return {
+    id: row.id,
+    companyId: row.companyId,
+    issueId: row.issueId,
+    key: row.key,
+    title: row.title,
+    format: row.format,
+    ...(includeBody ? { body: row.latestBody } : {}),
+    latestRevisionId: row.latestRevisionId ?? null,
+    latestRevisionNumber: row.latestRevisionNumber,
+    createdByAgentId: row.createdByAgentId,
+    createdByUserId: row.createdByUserId,
+    updatedByAgentId: row.updatedByAgentId,
+    updatedByUserId: row.updatedByUserId,
+    createdAt: row.createdAt,
+    updatedAt: row.updatedAt,
+  };
+}
+
+export function documentService(db: Db) {
+  return {
+    getIssueDocumentPayload: async (issue: { id: string; description: string | null }) => {
+      const [planDocument, documentSummaries] = await Promise.all([
+        db
+          .select({
+            id: documents.id,
+            companyId: documents.companyId,
+            issueId: issueDocuments.issueId,
+            key: issueDocuments.key,
+            title: documents.title,
+            format: documents.format,
+            latestBody: documents.latestBody,
+            latestRevisionId: documents.latestRevisionId,
+            latestRevisionNumber: documents.latestRevisionNumber,
+            createdByAgentId: documents.createdByAgentId,
+            createdByUserId: documents.createdByUserId,
+            updatedByAgentId: documents.updatedByAgentId,
+            updatedByUserId: documents.updatedByUserId,
+            createdAt: documents.createdAt,
+            updatedAt: documents.updatedAt,
+          })
+          .from(issueDocuments)
+          .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+          .where(and(eq(issueDocuments.issueId, issue.id), eq(issueDocuments.key, "plan")))
+          .then((rows) => rows[0] ?? null),
+        db
+          .select({
+            id: documents.id,
+            companyId: documents.companyId,
+            issueId: issueDocuments.issueId,
+            key: issueDocuments.key,
+            title: documents.title,
+            format: documents.format,
+            latestBody: documents.latestBody,
+            latestRevisionId: documents.latestRevisionId,
+            latestRevisionNumber: documents.latestRevisionNumber,
+            createdByAgentId: documents.createdByAgentId,
+            createdByUserId: documents.createdByUserId,
+            updatedByAgentId: documents.updatedByAgentId,
+            updatedByUserId: documents.updatedByUserId,
+            createdAt: documents.createdAt,
+            updatedAt: documents.updatedAt,
+          })
+          .from(issueDocuments)
+          .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+          .where(eq(issueDocuments.issueId, issue.id))
+          .orderBy(asc(issueDocuments.key), desc(documents.updatedAt)),
+      ]);
+
+      const legacyPlanBody = planDocument ? null : extractLegacyPlanBody(issue.description);
+
+      return {
+        planDocument: planDocument ? mapIssueDocumentRow(planDocument, true) : null,
+        documentSummaries: documentSummaries.map((row) => mapIssueDocumentRow(row, false)),
+        legacyPlanDocument: legacyPlanBody
+          ? {
+              key: "plan" as const,
+              body: legacyPlanBody,
+              source: "issue_description" as const,
+            }
+          : null,
+      };
+    },
+
+    listIssueDocuments: async (issueId: string) => {
+      const rows = await db
+        .select({
+          id: documents.id,
+          companyId: documents.companyId,
+          issueId: issueDocuments.issueId,
+          key: issueDocuments.key,
+          title: documents.title,
+          format: documents.format,
+          latestBody: documents.latestBody,
+          latestRevisionId: documents.latestRevisionId,
+          latestRevisionNumber: documents.latestRevisionNumber,
+          createdByAgentId: documents.createdByAgentId,
+          createdByUserId: documents.createdByUserId,
+          updatedByAgentId: documents.updatedByAgentId,
+          updatedByUserId: documents.updatedByUserId,
+          createdAt: documents.createdAt,
+          updatedAt: documents.updatedAt,
+        })
+        .from(issueDocuments)
+        .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+        .where(eq(issueDocuments.issueId, issueId))
+        .orderBy(asc(issueDocuments.key), desc(documents.updatedAt));
+      return rows.map((row) => mapIssueDocumentRow(row, true));
+    },
+
+    getIssueDocumentByKey: async (issueId: string, rawKey: string) => {
+      const key = normalizeDocumentKey(rawKey);
+      const row = await db
+        .select({
+          id: documents.id,
+          companyId: documents.companyId,
+          issueId: issueDocuments.issueId,
+          key: issueDocuments.key,
+          title: documents.title,
+          format: documents.format,
+          latestBody: documents.latestBody,
+          latestRevisionId: documents.latestRevisionId,
+          latestRevisionNumber: documents.latestRevisionNumber,
+          createdByAgentId: documents.createdByAgentId,
+          createdByUserId: documents.createdByUserId,
+          updatedByAgentId: documents.updatedByAgentId,
+          updatedByUserId: documents.updatedByUserId,
+          createdAt: documents.createdAt,
+          updatedAt: documents.updatedAt,
+        })
+        .from(issueDocuments)
+        .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+        .where(and(eq(issueDocuments.issueId, issueId), eq(issueDocuments.key, key)))
+        .then((rows) => rows[0] ?? null);
+      return row ? mapIssueDocumentRow(row, true) : null;
+    },
+
+    listIssueDocumentRevisions: async (issueId: string, rawKey: string) => {
+      const key = normalizeDocumentKey(rawKey);
+      return db
+        .select({
+          id: documentRevisions.id,
+          companyId: documentRevisions.companyId,
+          documentId: documentRevisions.documentId,
+          issueId: issueDocuments.issueId,
+          key: issueDocuments.key,
+          revisionNumber: documentRevisions.revisionNumber,
+          body: documentRevisions.body,
+          changeSummary: documentRevisions.changeSummary,
+          createdByAgentId: documentRevisions.createdByAgentId,
+          createdByUserId: documentRevisions.createdByUserId,
+          createdAt: documentRevisions.createdAt,
+        })
+        .from(issueDocuments)
+        .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+        .innerJoin(documentRevisions, eq(documentRevisions.documentId, documents.id))
+        .where(and(eq(issueDocuments.issueId, issueId), eq(issueDocuments.key, key)))
+        .orderBy(desc(documentRevisions.revisionNumber));
+    },
+
+    upsertIssueDocument: async (input: {
+      issueId: string;
+      key: string;
+      title?: string | null;
+      format: string;
+      body: string;
+      changeSummary?: string | null;
+      baseRevisionId?: string | null;
+      createdByAgentId?: string | null;
+      createdByUserId?: string | null;
+    }) => {
+      const key = normalizeDocumentKey(input.key);
+      const issue = await db
+        .select({ id: issues.id, companyId: issues.companyId })
+        .from(issues)
+        .where(eq(issues.id, input.issueId))
+        .then((rows) => rows[0] ?? null);
+      if (!issue) throw notFound("Issue not found");
+
+      try {
+        return await db.transaction(async (tx) => {
+          const now = new Date();
+          const existing = await tx
+            .select({
+              id: documents.id,
+              companyId: documents.companyId,
+              issueId: issueDocuments.issueId,
+              key: issueDocuments.key,
+              title: documents.title,
+              format: documents.format,
+              latestBody: documents.latestBody,
+              latestRevisionId: documents.latestRevisionId,
+              latestRevisionNumber: documents.latestRevisionNumber,
+              createdByAgentId: documents.createdByAgentId,
+              createdByUserId: documents.createdByUserId,
+              updatedByAgentId: documents.updatedByAgentId,
+              updatedByUserId: documents.updatedByUserId,
+              createdAt: documents.createdAt,
+              updatedAt: documents.updatedAt,
+            })
+            .from(issueDocuments)
+            .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+            .where(and(eq(issueDocuments.issueId, issue.id), eq(issueDocuments.key, key)))
+            .then((rows) => rows[0] ?? null);
+
+          if (existing) {
+            if (!input.baseRevisionId) {
+              throw conflict("Document update requires baseRevisionId", {
+                currentRevisionId: existing.latestRevisionId,
+              });
+            }
+            if (input.baseRevisionId !== existing.latestRevisionId) {
+              throw conflict("Document was updated by someone else", {
+                currentRevisionId: existing.latestRevisionId,
+              });
+            }
+
+            const nextRevisionNumber = existing.latestRevisionNumber + 1;
+            const [revision] = await tx
+              .insert(documentRevisions)
+              .values({
+                companyId: issue.companyId,
+                documentId: existing.id,
+                revisionNumber: nextRevisionNumber,
+                body: input.body,
+                changeSummary: input.changeSummary ?? null,
+                createdByAgentId: input.createdByAgentId ?? null,
+                createdByUserId: input.createdByUserId ?? null,
+                createdAt: now,
+              })
+              .returning();
+
+            await tx
+              .update(documents)
+              .set({
+                title: input.title ?? null,
+                format: input.format,
+                latestBody: input.body,
+                latestRevisionId: revision.id,
+                latestRevisionNumber: nextRevisionNumber,
+                updatedByAgentId: input.createdByAgentId ?? null,
+                updatedByUserId: input.createdByUserId ?? null,
+                updatedAt: now,
+              })
+              .where(eq(documents.id, existing.id));
+
+            await tx
+              .update(issueDocuments)
+              .set({ updatedAt: now })
+              .where(eq(issueDocuments.documentId, existing.id));
+
+            return {
+              created: false as const,
+              document: {
+                ...existing,
+                title: input.title ?? null,
+                format: input.format,
+                body: input.body,
+                latestRevisionId: revision.id,
+                latestRevisionNumber: nextRevisionNumber,
+                updatedByAgentId: input.createdByAgentId ?? null,
+                updatedByUserId: input.createdByUserId ?? null,
+                updatedAt: now,
+              },
+            };
+          }
+
+          if (input.baseRevisionId) {
+            throw conflict("Document does not exist yet", { key });
+          }
+
+          const [document] = await tx
+            .insert(documents)
+            .values({
+              companyId: issue.companyId,
+              title: input.title ?? null,
+              format: input.format,
+              latestBody: input.body,
+              latestRevisionId: null,
+              latestRevisionNumber: 1,
+              createdByAgentId: input.createdByAgentId ?? null,
+              createdByUserId: input.createdByUserId ?? null,
+              updatedByAgentId: input.createdByAgentId ?? null,
+              updatedByUserId: input.createdByUserId ?? null,
+              createdAt: now,
+              updatedAt: now,
+            })
+            .returning();
+
+          const [revision] = await tx
+            .insert(documentRevisions)
+            .values({
+              companyId: issue.companyId,
+              documentId: document.id,
+              revisionNumber: 1,
+              body: input.body,
+              changeSummary: input.changeSummary ?? null,
+              createdByAgentId: input.createdByAgentId ?? null,
+              createdByUserId: input.createdByUserId ?? null,
+              createdAt: now,
+            })
+            .returning();
+
+          await tx
+            .update(documents)
+            .set({ latestRevisionId: revision.id })
+            .where(eq(documents.id, document.id));
+
+          await tx.insert(issueDocuments).values({
+            companyId: issue.companyId,
+            issueId: issue.id,
+            documentId: document.id,
+            key,
+            createdAt: now,
+            updatedAt: now,
+          });
+
+          return {
+            created: true as const,
+            document: {
+              id: document.id,
+              companyId: issue.companyId,
+              issueId: issue.id,
+              key,
+              title: document.title,
+              format: document.format,
+              body: document.latestBody,
+              latestRevisionId: revision.id,
+              latestRevisionNumber: 1,
+              createdByAgentId: document.createdByAgentId,
+              createdByUserId: document.createdByUserId,
+              updatedByAgentId: document.updatedByAgentId,
+              updatedByUserId: document.updatedByUserId,
+              createdAt: document.createdAt,
+              updatedAt: document.updatedAt,
+            },
+          };
+        });
+      } catch (error) {
+        if (isUniqueViolation(error)) {
+          throw conflict("Document key already exists on this issue", { key });
+        }
+        throw error;
+      }
+    },
+
+    deleteIssueDocument: async (issueId: string, rawKey: string) => {
+      const key = normalizeDocumentKey(rawKey);
+      return db.transaction(async (tx) => {
+        const existing = await tx
+          .select({
+            id: documents.id,
+            companyId: documents.companyId,
+            issueId: issueDocuments.issueId,
+            key: issueDocuments.key,
+            title: documents.title,
+            format: documents.format,
+            latestBody: documents.latestBody,
+            latestRevisionId: documents.latestRevisionId,
+            latestRevisionNumber: documents.latestRevisionNumber,
+            createdByAgentId: documents.createdByAgentId,
+            createdByUserId: documents.createdByUserId,
+            updatedByAgentId: documents.updatedByAgentId,
+            updatedByUserId: documents.updatedByUserId,
+            createdAt: documents.createdAt,
+            updatedAt: documents.updatedAt,
+          })
+          .from(issueDocuments)
+          .innerJoin(documents, eq(issueDocuments.documentId, documents.id))
+          .where(and(eq(issueDocuments.issueId, issueId), eq(issueDocuments.key, key)))
+          .then((rows) => rows[0] ?? null);
+
+        if (!existing) return null;
+
+        await tx.delete(issueDocuments).where(eq(issueDocuments.documentId, existing.id));
+        await tx.delete(documents).where(eq(documents.id, existing.id));
+
+        return {
+          ...existing,
+          body: existing.latestBody,
+          latestRevisionId: existing.latestRevisionId ?? null,
+        };
+      });
+    },
+  };
+}

server/src/services/heartbeat.ts

@@ -18,7 +18,7 @@ import { logger } from "../middleware/logger.js";
 import { publishLiveEvent } from "./live-events.js";
 import { getRunLogStore, type RunLogHandle } from "./run-log-store.js";
 import { getServerAdapter, runningProcesses } from "../adapters/index.js";
-import type { AdapterExecutionResult, AdapterInvocationMeta, AdapterSessionCodec } from "../adapters/index.js";
+import type { AdapterExecutionResult, AdapterInvocationMeta, AdapterSessionCodec, UsageSummary } from "../adapters/index.js";
 import { createLocalAgentJwt } from "../agent-auth-jwt.js";
 import { parseObject, asBoolean, asNumber, appendWithCap, MAX_EXCERPT_BYTES } from "../adapters/utils.js";
 import { costService } from "./costs.js";
@@ -47,6 +47,14 @@ const HEARTBEAT_MAX_CONCURRENT_RUNS_MAX = 10;
 const DEFERRED_WAKE_CONTEXT_KEY = "_paperclipWakeContext";
 const startLocksByAgent = new Map<string, Promise<void>>();
 const REPO_ONLY_CWD_SENTINEL = "/__paperclip_repo_only__";
+const SESSIONED_LOCAL_ADAPTERS = new Set([
+  "claude_local",
+  "codex_local",
+  "cursor",
+  "gemini_local",
+  "opencode_local",
+  "pi_local",
+]);
 
 const heartbeatRunListColumns = {
   id: heartbeatRuns.id,
@@ -117,6 +125,26 @@ interface WakeupOptions {
   contextSnapshot?: Record<string, unknown>;
 }
 
+type UsageTotals = {
+  inputTokens: number;
+  cachedInputTokens: number;
+  outputTokens: number;
+};
+
+type SessionCompactionPolicy = {
+  enabled: boolean;
+  maxSessionRuns: number;
+  maxRawInputTokens: number;
+  maxSessionAgeHours: number;
+};
+
+type SessionCompactionDecision = {
+  rotate: boolean;
+  reason: string | null;
+  handoffMarkdown: string | null;
+  previousRunId: string | null;
+};
+
 interface ParsedIssueAssigneeAdapterOverrides {
   adapterConfig: Record<string, unknown> | null;
   useProjectWorkspace: boolean | null;
@@ -142,6 +170,88 @@ function readNonEmptyString(value: unknown): string | null {
   return typeof value === "string" && value.trim().length > 0 ? value : null;
 }
 
+function normalizeUsageTotals(usage: UsageSummary | null | undefined): UsageTotals | null {
+  if (!usage) return null;
+  return {
+    inputTokens: Math.max(0, Math.floor(asNumber(usage.inputTokens, 0))),
+    cachedInputTokens: Math.max(0, Math.floor(asNumber(usage.cachedInputTokens, 0))),
+    outputTokens: Math.max(0, Math.floor(asNumber(usage.outputTokens, 0))),
+  };
+}
+
+function readRawUsageTotals(usageJson: unknown): UsageTotals | null {
+  const parsed = parseObject(usageJson);
+  if (Object.keys(parsed).length === 0) return null;
+
+  const inputTokens = Math.max(
+    0,
+    Math.floor(asNumber(parsed.rawInputTokens, asNumber(parsed.inputTokens, 0))),
+  );
+  const cachedInputTokens = Math.max(
+    0,
+    Math.floor(asNumber(parsed.rawCachedInputTokens, asNumber(parsed.cachedInputTokens, 0))),
+  );
+  const outputTokens = Math.max(
+    0,
+    Math.floor(asNumber(parsed.rawOutputTokens, asNumber(parsed.outputTokens, 0))),
+  );
+
+  if (inputTokens <= 0 && cachedInputTokens <= 0 && outputTokens <= 0) {
+    return null;
+  }
+
+  return {
+    inputTokens,
+    cachedInputTokens,
+    outputTokens,
+  };
+}
+
+function deriveNormalizedUsageDelta(current: UsageTotals | null, previous: UsageTotals | null): UsageTotals | null {
+  if (!current) return null;
+  if (!previous) return { ...current };
+
+  const inputTokens = current.inputTokens >= previous.inputTokens
+    ? current.inputTokens - previous.inputTokens
+    : current.inputTokens;
+  const cachedInputTokens = current.cachedInputTokens >= previous.cachedInputTokens
+    ? current.cachedInputTokens - previous.cachedInputTokens
+    : current.cachedInputTokens;
+  const outputTokens = current.outputTokens >= previous.outputTokens
+    ? current.outputTokens - previous.outputTokens
+    : current.outputTokens;
+
+  return {
+    inputTokens: Math.max(0, inputTokens),
+    cachedInputTokens: Math.max(0, cachedInputTokens),
+    outputTokens: Math.max(0, outputTokens),
+  };
+}
+
+function formatCount(value: number | null | undefined) {
+  if (typeof value !== "number" || !Number.isFinite(value)) return "0";
+  return value.toLocaleString("en-US");
+}
+
+function parseSessionCompactionPolicy(agent: typeof agents.$inferSelect): SessionCompactionPolicy {
+  const runtimeConfig = parseObject(agent.runtimeConfig);
+  const heartbeat = parseObject(runtimeConfig.heartbeat);
+  const compaction = parseObject(
+    heartbeat.sessionCompaction ?? heartbeat.sessionRotation ?? runtimeConfig.sessionCompaction,
+  );
+  const supportsSessions = SESSIONED_LOCAL_ADAPTERS.has(agent.adapterType);
+  const enabled = compaction.enabled === undefined
+    ? supportsSessions
+    : asBoolean(compaction.enabled, supportsSessions);
+
+  return {
+    enabled,
+    maxSessionRuns: Math.max(0, Math.floor(asNumber(compaction.maxSessionRuns, 200))),
+    maxRawInputTokens: Math.max(0, Math.floor(asNumber(compaction.maxRawInputTokens, 2_000_000))),
+    maxSessionAgeHours: Math.max(0, Math.floor(asNumber(compaction.maxSessionAgeHours, 72))),
+  };
+}
+
 export function resolveRuntimeSessionParamsForWorkspace(input: {
   agentId: string;
   previousSessionParams: Record<string, unknown> | null;
@@ -246,29 +356,20 @@ function deriveTaskKey(
 export function shouldResetTaskSessionForWake(
   contextSnapshot: Record<string, unknown> | null | undefined,
 ) {
+  if (contextSnapshot?.forceFreshSession === true) return true;
+
   const wakeReason = readNonEmptyString(contextSnapshot?.wakeReason);
   if (wakeReason === "issue_assigned") return true;
-
-  const wakeSource = readNonEmptyString(contextSnapshot?.wakeSource);
-  if (wakeSource === "timer") return true;
-
-  const wakeTriggerDetail = readNonEmptyString(contextSnapshot?.wakeTriggerDetail);
-  return wakeSource === "on_demand" && wakeTriggerDetail === "manual";
+  return false;
 }
 
 function describeSessionResetReason(
   contextSnapshot: Record<string, unknown> | null | undefined,
 ) {
+  if (contextSnapshot?.forceFreshSession === true) return "forceFreshSession was requested";
+
   const wakeReason = readNonEmptyString(contextSnapshot?.wakeReason);
   if (wakeReason === "issue_assigned") return "wake reason is issue_assigned";
-
-  const wakeSource = readNonEmptyString(contextSnapshot?.wakeSource);
-  if (wakeSource === "timer") return "wake source is timer";
-
-  const wakeTriggerDetail = readNonEmptyString(contextSnapshot?.wakeTriggerDetail);
-  if (wakeSource === "on_demand" && wakeTriggerDetail === "manual") {
-    return "this is a manual invoke";
-  }
   return null;
 }
 
@@ -501,6 +602,176 @@ export function heartbeatService(db: Db) {
       .then((rows) => rows[0] ?? null);
   }
 
+  async function getLatestRunForSession(
+    agentId: string,
+    sessionId: string,
+    opts?: { excludeRunId?: string | null },
+  ) {
+    const conditions = [
+      eq(heartbeatRuns.agentId, agentId),
+      eq(heartbeatRuns.sessionIdAfter, sessionId),
+    ];
+    if (opts?.excludeRunId) {
+      conditions.push(sql`${heartbeatRuns.id} <> ${opts.excludeRunId}`);
+    }
+    return db
+      .select()
+      .from(heartbeatRuns)
+      .where(and(...conditions))
+      .orderBy(desc(heartbeatRuns.createdAt))
+      .limit(1)
+      .then((rows) => rows[0] ?? null);
+  }
+
+  async function getOldestRunForSession(agentId: string, sessionId: string) {
+    return db
+      .select({
+        id: heartbeatRuns.id,
+        createdAt: heartbeatRuns.createdAt,
+      })
+      .from(heartbeatRuns)
+      .where(and(eq(heartbeatRuns.agentId, agentId), eq(heartbeatRuns.sessionIdAfter, sessionId)))
+      .orderBy(asc(heartbeatRuns.createdAt), asc(heartbeatRuns.id))
+      .limit(1)
+      .then((rows) => rows[0] ?? null);
+  }
+
+  async function resolveNormalizedUsageForSession(input: {
+    agentId: string;
+    runId: string;
+    sessionId: string | null;
+    rawUsage: UsageTotals | null;
+  }) {
+    const { agentId, runId, sessionId, rawUsage } = input;
+    if (!sessionId || !rawUsage) {
+      return {
+        normalizedUsage: rawUsage,
+        previousRawUsage: null as UsageTotals | null,
+        derivedFromSessionTotals: false,
+      };
+    }
+
+    const previousRun = await getLatestRunForSession(agentId, sessionId, { excludeRunId: runId });
+    const previousRawUsage = readRawUsageTotals(previousRun?.usageJson);
+    return {
+      normalizedUsage: deriveNormalizedUsageDelta(rawUsage, previousRawUsage),
+      previousRawUsage,
+      derivedFromSessionTotals: previousRawUsage !== null,
+    };
+  }
+
+  async function evaluateSessionCompaction(input: {
+    agent: typeof agents.$inferSelect;
+    sessionId: string | null;
+    issueId: string | null;
+  }): Promise<SessionCompactionDecision> {
+    const { agent, sessionId, issueId } = input;
+    if (!sessionId) {
+      return {
+        rotate: false,
+        reason: null,
+        handoffMarkdown: null,
+        previousRunId: null,
+      };
+    }
+
+    const policy = parseSessionCompactionPolicy(agent);
+    if (!policy.enabled) {
+      return {
+        rotate: false,
+        reason: null,
+        handoffMarkdown: null,
+        previousRunId: null,
+      };
+    }
+
+    const fetchLimit = Math.max(policy.maxSessionRuns > 0 ? policy.maxSessionRuns + 1 : 0, 4);
+    const runs = await db
+      .select({
+        id: heartbeatRuns.id,
+        createdAt: heartbeatRuns.createdAt,
+        usageJson: heartbeatRuns.usageJson,
+        resultJson: heartbeatRuns.resultJson,
+        error: heartbeatRuns.error,
+      })
+      .from(heartbeatRuns)
+      .where(and(eq(heartbeatRuns.agentId, agent.id), eq(heartbeatRuns.sessionIdAfter, sessionId)))
+      .orderBy(desc(heartbeatRuns.createdAt))
+      .limit(fetchLimit);
+
+    if (runs.length === 0) {
+      return {
+        rotate: false,
+        reason: null,
+        handoffMarkdown: null,
+        previousRunId: null,
+      };
+    }
+
+    const latestRun = runs[0] ?? null;
+    const oldestRun =
+      policy.maxSessionAgeHours > 0
+        ? await getOldestRunForSession(agent.id, sessionId)
+        : runs[runs.length - 1] ?? latestRun;
+    const latestRawUsage = readRawUsageTotals(latestRun?.usageJson);
+    const sessionAgeHours =
+      latestRun && oldestRun
+        ? Math.max(
+            0,
+            (new Date(latestRun.createdAt).getTime() - new Date(oldestRun.createdAt).getTime()) / (1000 * 60 * 60),
+          )
+        : 0;
+
+    let reason: string | null = null;
+    if (policy.maxSessionRuns > 0 && runs.length > policy.maxSessionRuns) {
+      reason = `session exceeded ${policy.maxSessionRuns} runs`;
+    } else if (
+      policy.maxRawInputTokens > 0 &&
+      latestRawUsage &&
+      latestRawUsage.inputTokens >= policy.maxRawInputTokens
+    ) {
+      reason =
+        `session raw input reached ${formatCount(latestRawUsage.inputTokens)} tokens ` +
+        `(threshold ${formatCount(policy.maxRawInputTokens)})`;
+    } else if (policy.maxSessionAgeHours > 0 && sessionAgeHours >= policy.maxSessionAgeHours) {
+      reason = `session age reached ${Math.floor(sessionAgeHours)} hours`;
+    }
+
+    if (!reason || !latestRun) {
+      return {
+        rotate: false,
+        reason: null,
+        handoffMarkdown: null,
+        previousRunId: latestRun?.id ?? null,
+      };
+    }
+
+    const latestSummary = summarizeHeartbeatRunResultJson(latestRun.resultJson);
+    const latestTextSummary =
+      readNonEmptyString(latestSummary?.summary) ??
+      readNonEmptyString(latestSummary?.result) ??
+      readNonEmptyString(latestSummary?.message) ??
+      readNonEmptyString(latestRun.error);
+
+    const handoffMarkdown = [
+      "Paperclip session handoff:",
+      `- Previous session: ${sessionId}`,
+      issueId ? `- Issue: ${issueId}` : "",
+      `- Rotation reason: ${reason}`,
+      latestTextSummary ? `- Last run summary: ${latestTextSummary}` : "",
+      "Continue from the current task state. Rebuild only the minimum context you need.",
+    ]
+      .filter(Boolean)
+      .join("\n");
+
+    return {
+      rotate: true,
+      reason,
+      handoffMarkdown,
+      previousRunId: latestRun.id,
+    };
+  }
+
   async function resolveSessionBeforeForWakeup(
     agent: typeof agents.$inferSelect,
     taskKey: string | null,
@@ -1016,9 +1287,10 @@ export function heartbeatService(db: Db) {
     run: typeof heartbeatRuns.$inferSelect,
     result: AdapterExecutionResult,
     session: { legacySessionId: string | null },
+    normalizedUsage?: UsageTotals | null,
   ) {
     await ensureRuntimeState(agent);
-    const usage = result.usage;
+    const usage = normalizedUsage ?? normalizeUsageTotals(result.usage);
     const inputTokens = usage?.inputTokens ?? 0;
     const outputTokens = usage?.outputTokens ?? 0;
     const cachedInputTokens = usage?.cachedInputTokens ?? 0;
@@ -1270,15 +1542,42 @@ export function heartbeatService(db: Db) {
       context.projectId = executionWorkspace.projectId;
     }
     const runtimeSessionFallback = taskKey || resetTaskSession ? null : runtime.sessionId;
-    const previousSessionDisplayId = truncateDisplayId(
+    let previousSessionDisplayId = truncateDisplayId(
       taskSessionForRun?.sessionDisplayId ??
         (sessionCodec.getDisplayId ? sessionCodec.getDisplayId(runtimeSessionParams) : null) ??
         readNonEmptyString(runtimeSessionParams?.sessionId) ??
         runtimeSessionFallback,
     );
+    let runtimeSessionIdForAdapter =
+      readNonEmptyString(runtimeSessionParams?.sessionId) ?? runtimeSessionFallback;
+    let runtimeSessionParamsForAdapter = runtimeSessionParams;
+
+    const sessionCompaction = await evaluateSessionCompaction({
+      agent,
+      sessionId: previousSessionDisplayId ?? runtimeSessionIdForAdapter,
+      issueId,
+    });
+    if (sessionCompaction.rotate) {
+      context.paperclipSessionHandoffMarkdown = sessionCompaction.handoffMarkdown;
+      context.paperclipSessionRotationReason = sessionCompaction.reason;
+      context.paperclipPreviousSessionId = previousSessionDisplayId ?? runtimeSessionIdForAdapter;
+      runtimeSessionIdForAdapter = null;
+      runtimeSessionParamsForAdapter = null;
+      previousSessionDisplayId = null;
+      if (sessionCompaction.reason) {
+        runtimeWorkspaceWarnings.push(
+          `Starting a fresh session because ${sessionCompaction.reason}.`,
+        );
+      }
+    } else {
+      delete context.paperclipSessionHandoffMarkdown;
+      delete context.paperclipSessionRotationReason;
+      delete context.paperclipPreviousSessionId;
+    }
+
     const runtimeForAdapter = {
-      sessionId: readNonEmptyString(runtimeSessionParams?.sessionId) ?? runtimeSessionFallback,
-      sessionParams: runtimeSessionParams,
+      sessionId: runtimeSessionIdForAdapter,
+      sessionParams: runtimeSessionParamsForAdapter,
       sessionDisplayId: previousSessionDisplayId,
       taskKey,
     };
@@ -1522,6 +1821,14 @@ export function heartbeatService(db: Db) {
         previousDisplayId: runtimeForAdapter.sessionDisplayId,
         previousLegacySessionId: runtimeForAdapter.sessionId,
       });
+      const rawUsage = normalizeUsageTotals(adapterResult.usage);
+      const sessionUsageResolution = await resolveNormalizedUsageForSession({
+        agentId: agent.id,
+        runId: run.id,
+        sessionId: nextSessionState.displayId ?? nextSessionState.legacySessionId,
+        rawUsage,
+      });
+      const normalizedUsage = sessionUsageResolution.normalizedUsage;
 
       let outcome: "succeeded" | "failed" | "cancelled" | "timed_out";
       const latestRun = await getRun(run.id);
@@ -1550,9 +1857,23 @@ export function heartbeatService(db: Db) {
               : "failed";
 
       const usageJson =
-        adapterResult.usage || adapterResult.costUsd != null
+        normalizedUsage || adapterResult.costUsd != null
           ? ({
-              ...(adapterResult.usage ?? {}),
+              ...(normalizedUsage ?? {}),
+              ...(rawUsage ? {
+                rawInputTokens: rawUsage.inputTokens,
+                rawCachedInputTokens: rawUsage.cachedInputTokens,
+                rawOutputTokens: rawUsage.outputTokens,
+              } : {}),
+              ...(sessionUsageResolution.derivedFromSessionTotals ? { usageSource: "session_delta" } : {}),
+              ...((nextSessionState.displayId ?? nextSessionState.legacySessionId)
+                ? { persistedSessionId: nextSessionState.displayId ?? nextSessionState.legacySessionId }
+                : {}),
+              sessionReused: runtimeForAdapter.sessionId != null || runtimeForAdapter.sessionDisplayId != null,
+              taskSessionReused: taskSessionForRun != null,
+              freshSession: runtimeForAdapter.sessionId == null && runtimeForAdapter.sessionDisplayId == null,
+              sessionRotated: sessionCompaction.rotate,
+              sessionRotationReason: sessionCompaction.reason,
               ...(adapterResult.costUsd != null ? { costUsd: adapterResult.costUsd } : {}),
               ...(adapterResult.billingType ? { billingType: adapterResult.billingType } : {}),
             } as Record<string, unknown>)
@@ -1609,7 +1930,7 @@ export function heartbeatService(db: Db) {
       if (finalizedRun) {
         await updateRuntimeState(agent, finalizedRun, adapterResult, {
           legacySessionId: nextSessionState.legacySessionId,
-        });
+        }, normalizedUsage);
         if (taskKey) {
           if (adapterResult.clearSession || (!nextSessionState.params && !nextSessionState.displayId)) {
             await clearTaskSessions(agent.companyId, agent.id, {

server/src/services/index.ts

@@ -1,6 +1,7 @@
 export { companyService } from "./companies.js";
 export { agentService, deduplicateAgentName } from "./agents.js";
 export { assetService } from "./assets.js";
+export { documentService, extractLegacyPlanBody } from "./documents.js";
 export { projectService } from "./projects.js";
 export { issueService, type IssueFilters } from "./issues.js";
 export { issueApprovalService } from "./issue-approvals.js";

server/src/services/issues.ts

@@ -5,11 +5,13 @@ import {
   assets,
   companies,
   companyMemberships,
+  documents,
   goals,
   heartbeatRuns,
   issueAttachments,
   issueLabels,
   issueComments,
+  issueDocuments,
   issueReadStates,
   issues,
   labels,
@@ -27,6 +29,7 @@ import { resolveIssueGoalId, resolveNextIssueGoalId } from "./issue-goal-fallbac
 import { getDefaultCompanyGoal } from "./goals.js";
 
 const ALL_ISSUE_STATUSES = ["backlog", "todo", "in_progress", "in_review", "blocked", "done", "cancelled"];
+const MAX_ISSUE_COMMENT_PAGE_LIMIT = 500;
 
 function assertTransition(from: string, to: string) {
   if (from === to) return;
@@ -789,6 +792,10 @@ export function issueService(db: Db) {
           .select({ assetId: issueAttachments.assetId })
           .from(issueAttachments)
           .where(eq(issueAttachments.issueId, id));
+        const issueDocumentIds = await tx
+          .select({ documentId: issueDocuments.documentId })
+          .from(issueDocuments)
+          .where(eq(issueDocuments.issueId, id));
 
         const removedIssue = await tx
           .delete(issues)
@@ -802,6 +809,12 @@ export function issueService(db: Db) {
             .where(inArray(assets.id, attachmentAssetIds.map((row) => row.assetId)));
         }
 
+        if (removedIssue && issueDocumentIds.length > 0) {
+          await tx
+            .delete(documents)
+            .where(inArray(documents.id, issueDocumentIds.map((row) => row.documentId)));
+        }
+
         if (!removedIssue) return null;
         const [enriched] = await withIssueLabels(tx, [removedIssue]);
         return enriched;
@@ -1060,13 +1073,86 @@ export function issueService(db: Db) {
         .returning()
         .then((rows) => rows[0] ?? null),
 
-    listComments: (issueId: string) =>
-      db
+    listComments: async (
+      issueId: string,
+      opts?: {
+        afterCommentId?: string | null;
+        order?: "asc" | "desc";
+        limit?: number | null;
+      },
+    ) => {
+      const order = opts?.order === "asc" ? "asc" : "desc";
+      const afterCommentId = opts?.afterCommentId?.trim() || null;
+      const limit =
+        opts?.limit && opts.limit > 0
+          ? Math.min(Math.floor(opts.limit), MAX_ISSUE_COMMENT_PAGE_LIMIT)
+          : null;
+
+      const conditions = [eq(issueComments.issueId, issueId)];
+      if (afterCommentId) {
+        const anchor = await db
+          .select({
+            id: issueComments.id,
+            createdAt: issueComments.createdAt,
+          })
+          .from(issueComments)
+          .where(and(eq(issueComments.issueId, issueId), eq(issueComments.id, afterCommentId)))
+          .then((rows) => rows[0] ?? null);
+
+        if (!anchor) return [];
+        conditions.push(
+          order === "asc"
+            ? sql<boolean>`(
+                ${issueComments.createdAt} > ${anchor.createdAt}
+                OR (${issueComments.createdAt} = ${anchor.createdAt} AND ${issueComments.id} > ${anchor.id})
+              )`
+            : sql<boolean>`(
+                ${issueComments.createdAt} < ${anchor.createdAt}
+                OR (${issueComments.createdAt} = ${anchor.createdAt} AND ${issueComments.id} < ${anchor.id})
+              )`,
+        );
+      }
+
+      const query = db
         .select()
         .from(issueComments)
-        .where(eq(issueComments.issueId, issueId))
-        .orderBy(desc(issueComments.createdAt))
-        .then((comments) => comments.map(redactIssueComment)),
+        .where(and(...conditions))
+        .orderBy(
+          order === "asc" ? asc(issueComments.createdAt) : desc(issueComments.createdAt),
+          order === "asc" ? asc(issueComments.id) : desc(issueComments.id),
+        );
+
+      const comments = limit ? await query.limit(limit) : await query;
+      return comments.map(redactIssueComment);
+    },
+
+    getCommentCursor: async (issueId: string) => {
+      const [latest, countRow] = await Promise.all([
+        db
+          .select({
+            latestCommentId: issueComments.id,
+            latestCommentAt: issueComments.createdAt,
+          })
+          .from(issueComments)
+          .where(eq(issueComments.issueId, issueId))
+          .orderBy(desc(issueComments.createdAt), desc(issueComments.id))
+          .limit(1)
+          .then((rows) => rows[0] ?? null),
+        db
+          .select({
+            totalComments: sql<number>`count(*)::int`,
+          })
+          .from(issueComments)
+          .where(eq(issueComments.issueId, issueId))
+          .then((rows) => rows[0] ?? null),
+      ]);
+
+      return {
+        totalComments: Number(countRow?.totalComments ?? 0),
+        latestCommentId: latest?.latestCommentId ?? null,
+        latestCommentAt: latest?.latestCommentAt ?? null,
+      };
+    },
 
     getComment: (commentId: string) =>
       db

skills/paperclip/SKILL.md

@@ -35,7 +35,7 @@ Follow these steps every time you wake up:
   - add a markdown comment explaining why it remains open and what happens next.
     Always include links to the approval and issue in that comment.
 
-**Step 3 — Get assignments.** `GET /api/companies/{companyId}/issues?assigneeAgentId={your-agent-id}&status=todo,in_progress,blocked`. Results sorted by priority. This is your inbox.
+**Step 3 — Get assignments.** Prefer `GET /api/agents/me/inbox-lite` for the normal heartbeat inbox. It returns the compact assignment list you need for prioritization. Fall back to `GET /api/companies/{companyId}/issues?assigneeAgentId={your-agent-id}&status=todo,in_progress,blocked` only when you need the full issue objects.
 
 **Step 4 — Pick work (with mention exception).** Work on `in_progress` first, then `todo`. Skip `blocked` unless you can unblock it.
 **Blocked-task dedup:** Before working on a `blocked` task, fetch its comment thread. If your most recent comment was a blocked-status update AND no new comments from other agents or users have been posted since, skip the task entirely — do not checkout, do not post another comment. Exit the heartbeat (or move to the next task) instead. Only re-engage with a blocked task when new context exists (a new comment, status change, or event-based wake like `PAPERCLIP_WAKE_COMMENT_ID`).
@@ -56,8 +56,15 @@ Headers: Authorization: Bearer $PAPERCLIP_API_KEY, X-Paperclip-Run-Id: $PAPERCLI
 
 If already checked out by you, returns normally. If owned by another agent: `409 Conflict` — stop, pick a different task. **Never retry a 409.**
 
-**Step 6 — Understand context.** `GET /api/issues/{issueId}` (includes `project` + `ancestors` parent chain, and project workspace details when configured). `GET /api/issues/{issueId}/comments`. Read ancestors to understand _why_ this task exists.
-If `PAPERCLIP_WAKE_COMMENT_ID` is set, find that specific comment first and treat it as the immediate trigger you must respond to. Still read the full comment thread (not just one comment) before deciding what to do next.
+**Step 6 — Understand context.** Prefer `GET /api/issues/{issueId}/heartbeat-context` first. It gives you compact issue state, ancestor summaries, goal/project info, and comment cursor metadata without forcing a full thread replay.
+
+Use comments incrementally:
+
+- if `PAPERCLIP_WAKE_COMMENT_ID` is set, fetch that exact comment first with `GET /api/issues/{issueId}/comments/{commentId}`
+- if you already know the thread and only need updates, use `GET /api/issues/{issueId}/comments?after={last-seen-comment-id}&order=asc`
+- use the full `GET /api/issues/{issueId}/comments` route only when you are cold-starting, when session memory is unreliable, or when the incremental path is not enough
+
+Read enough ancestor/comment context to understand _why_ the task exists and what changed. Do not reflexively reload the whole thread on every heartbeat.
 
 **Step 7 — Do the work.** Use your tools and capabilities.
 
@@ -147,6 +154,7 @@ When posting issue comments, use concise markdown with:
 
 - Issues: `/<prefix>/issues/<issue-identifier>` (e.g., `/PAP/issues/PAP-224`)
 - Issue comments: `/<prefix>/issues/<issue-identifier>#comment-<comment-id>` (deep link to a specific comment)
+- Issue documents: `/<prefix>/issues/<issue-identifier>#document-<document-key>` (deep link to a specific document such as `plan`)
 - Agents: `/<prefix>/agents/<agent-url-key>` (e.g., `/PAP/agents/claudecoder`)
 - Projects: `/<prefix>/projects/<project-url-key>` (id fallback allowed)
 - Approvals: `/<prefix>/approvals/<approval-id>`
@@ -168,31 +176,30 @@ Submitted CTO hire request and linked it for board review.
 
 ## Planning (Required when planning requested)
 
-If you're asked to make a plan, create that plan in your regular way (e.g. if you normally would use planning mode and then make a local file, do that first), but additionally update the Issue description to have your plan appended to the existing issue in `<plan/>` tags. You MUST keep the original Issue description exactly in tact. ONLY add/edit your plan. If you're asked for plan revisions, update your `<plan/>` with the revision. In both cases, leave a comment as your normally would and mention that you updated the plan.
+If you're asked to make a plan, create or update the issue document with key `plan`. Do not append plans into the issue description anymore. If you're asked for plan revisions, update that same `plan` document. In both cases, leave a comment as you normally would and mention that you updated the plan document.
+
+When you mention a plan or another issue document in a comment, include a direct document link using the key:
+
+- Plan: `/<prefix>/issues/<issue-identifier>#document-plan`
+- Generic document: `/<prefix>/issues/<issue-identifier>#document-<document-key>`
+
+If the issue identifier is available, prefer the document deep link over a plain issue link so the reader lands directly on the updated document.
 
 If you're asked to make a plan, _do not mark the issue as done_. Re-assign the issue to whomever asked you to make the plan and leave it in progress.
 
-Example:
+Recommended API flow:
 
-Original Issue Description:
-
-```
-pls show the costs in either token or dollars on the /issues/{id} page. Make a plan first.
+```bash
+PUT /api/issues/{issueId}/documents/plan
+{
+  "title": "Plan",
+  "format": "markdown",
+  "body": "# Plan\n\n[your plan here]",
+  "baseRevisionId": null
+}
 ```
 
-After:
-
-```
-pls show the costs in either token or dollars on the /issues/{id} page. Make a plan first.
-
-<plan>
-
-[your plan here]
-
-</plan>
-```
-
-\*make sure to have a newline after/before your <plan/> tags
+If `plan` already exists, fetch the current document first and send its latest `baseRevisionId` when you update it.
 
 ## Setting Agent Instructions Path
 
@@ -226,10 +233,17 @@ PATCH /api/agents/{agentId}/instructions-path
 | Action                                | Endpoint                                                                                   |
 | ------------------------------------- | ------------------------------------------------------------------------------------------ |
 | My identity                           | `GET /api/agents/me`                                                                       |
+| My compact inbox                      | `GET /api/agents/me/inbox-lite`                                                            |
 | My assignments                        | `GET /api/companies/:companyId/issues?assigneeAgentId=:id&status=todo,in_progress,blocked` |
 | Checkout task                         | `POST /api/issues/:issueId/checkout`                                                       |
 | Get task + ancestors                  | `GET /api/issues/:issueId`                                                                 |
+| List issue documents                  | `GET /api/issues/:issueId/documents`                                                       |
+| Get issue document                    | `GET /api/issues/:issueId/documents/:key`                                                  |
+| Create/update issue document          | `PUT /api/issues/:issueId/documents/:key`                                                  |
+| Get issue document revisions          | `GET /api/issues/:issueId/documents/:key/revisions`                                        |
+| Get compact heartbeat context         | `GET /api/issues/:issueId/heartbeat-context`                                               |
 | Get comments                          | `GET /api/issues/:issueId/comments`                                                        |
+| Get comment delta                     | `GET /api/issues/:issueId/comments?after=:commentId&order=asc`                             |
 | Get specific comment                  | `GET /api/issues/:issueId/comments/:commentId`                                             |
 | Update task                           | `PATCH /api/issues/:issueId` (optional `comment` field)                                    |
 | Add comment                           | `POST /api/issues/:issueId/comments`                                                       |

ui/src/api/issues.ts

@@ -1,4 +1,13 @@
-import type { Approval, Issue, IssueAttachment, IssueComment, IssueLabel } from "@paperclipai/shared";
+import type {
+  Approval,
+  DocumentRevision,
+  Issue,
+  IssueAttachment,
+  IssueComment,
+  IssueDocument,
+  IssueLabel,
+  UpsertIssueDocument,
+} from "@paperclipai/shared";
 import { api } from "./client";
 
 export const issuesApi = {
@@ -53,6 +62,14 @@ export const issuesApi = {
         ...(interrupt === undefined ? {} : { interrupt }),
       },
     ),
+  listDocuments: (id: string) => api.get<IssueDocument[]>(`/issues/${id}/documents`),
+  getDocument: (id: string, key: string) => api.get<IssueDocument>(`/issues/${id}/documents/${encodeURIComponent(key)}`),
+  upsertDocument: (id: string, key: string, data: UpsertIssueDocument) =>
+    api.put<IssueDocument>(`/issues/${id}/documents/${encodeURIComponent(key)}`, data),
+  listDocumentRevisions: (id: string, key: string) =>
+    api.get<DocumentRevision[]>(`/issues/${id}/documents/${encodeURIComponent(key)}/revisions`),
+  deleteDocument: (id: string, key: string) =>
+    api.delete<{ ok: true }>(`/issues/${id}/documents/${encodeURIComponent(key)}`),
   listAttachments: (id: string) => api.get<IssueAttachment[]>(`/issues/${id}/attachments`),
   uploadAttachment: (
     companyId: string,

ui/src/components/ActivityRow.tsx

@@ -12,6 +12,9 @@ const ACTION_VERBS: Record<string, string> = {
   "issue.comment_added": "commented on",
   "issue.attachment_added": "attached file to",
   "issue.attachment_removed": "removed attachment from",
+  "issue.document_created": "created document for",
+  "issue.document_updated": "updated document on",
+  "issue.document_deleted": "deleted document from",
   "issue.commented": "commented on",
   "issue.deleted": "deleted",
   "agent.created": "created",

ui/src/components/AgentConfigForm.tsx

@@ -444,23 +444,28 @@ export function AgentConfigForm(props: AgentConfigFormProps) {
               />
             </Field>
             {isLocal && (
-              <Field label="Prompt Template" hint={help.promptTemplate}>
-                <MarkdownEditor
-                  value={eff(
-                    "adapterConfig",
-                    "promptTemplate",
-                    String(config.promptTemplate ?? ""),
-                  )}
-                  onChange={(v) => mark("adapterConfig", "promptTemplate", v ?? "")}
-                  placeholder="You are agent {{ agent.name }}. Your role is {{ agent.role }}..."
-                  contentClassName="min-h-[88px] text-sm font-mono"
-                  imageUploadHandler={async (file) => {
-                    const namespace = `agents/${props.agent.id}/prompt-template`;
-                    const asset = await uploadMarkdownImage.mutateAsync({ file, namespace });
-                    return asset.contentPath;
-                  }}
-                />
-              </Field>
+              <>
+                <Field label="Prompt Template" hint={help.promptTemplate}>
+                  <MarkdownEditor
+                    value={eff(
+                      "adapterConfig",
+                      "promptTemplate",
+                      String(config.promptTemplate ?? ""),
+                    )}
+                    onChange={(v) => mark("adapterConfig", "promptTemplate", v ?? "")}
+                    placeholder="You are agent {{ agent.name }}. Your role is {{ agent.role }}..."
+                    contentClassName="min-h-[88px] text-sm font-mono"
+                    imageUploadHandler={async (file) => {
+                      const namespace = `agents/${props.agent.id}/prompt-template`;
+                      const asset = await uploadMarkdownImage.mutateAsync({ file, namespace });
+                      return asset.contentPath;
+                    }}
+                  />
+                </Field>
+                <div className="rounded-md border border-amber-500/25 bg-amber-500/10 px-3 py-2 text-xs text-amber-100">
+                  Prompt template is replayed on every heartbeat. Keep it compact and dynamic to avoid recurring token cost and cache churn.
+                </div>
+              </>
             )}
           </div>
         </div>
@@ -576,19 +581,24 @@ export function AgentConfigForm(props: AgentConfigFormProps) {
 
           {/* Prompt template (create mode only — edit mode shows this in Identity) */}
           {isLocal && isCreate && (
-            <Field label="Prompt Template" hint={help.promptTemplate}>
-              <MarkdownEditor
-                value={val!.promptTemplate}
-                onChange={(v) => set!({ promptTemplate: v })}
-                placeholder="You are agent {{ agent.name }}. Your role is {{ agent.role }}..."
-                contentClassName="min-h-[88px] text-sm font-mono"
-                imageUploadHandler={async (file) => {
-                  const namespace = "agents/drafts/prompt-template";
-                  const asset = await uploadMarkdownImage.mutateAsync({ file, namespace });
-                  return asset.contentPath;
-                }}
-              />
-            </Field>
+            <>
+              <Field label="Prompt Template" hint={help.promptTemplate}>
+                <MarkdownEditor
+                  value={val!.promptTemplate}
+                  onChange={(v) => set!({ promptTemplate: v })}
+                  placeholder="You are agent {{ agent.name }}. Your role is {{ agent.role }}..."
+                  contentClassName="min-h-[88px] text-sm font-mono"
+                  imageUploadHandler={async (file) => {
+                    const namespace = "agents/drafts/prompt-template";
+                    const asset = await uploadMarkdownImage.mutateAsync({ file, namespace });
+                    return asset.contentPath;
+                  }}
+                />
+              </Field>
+              <div className="rounded-md border border-amber-500/25 bg-amber-500/10 px-3 py-2 text-xs text-amber-100">
+                Prompt template is replayed on every heartbeat. Prefer small task framing and variables like <code>{"{{ context.* }}"}</code> or <code>{"{{ run.* }}"}</code>; avoid repeating stable instructions here.
+              </div>
+            </>
           )}
 
           {/* Adapter-specific fields */}
@@ -704,6 +714,9 @@ export function AgentConfigForm(props: AgentConfigFormProps) {
                   }}
                 />
               </Field>
+              <div className="rounded-md border border-sky-500/25 bg-sky-500/10 px-3 py-2 text-xs text-sky-100">
+                Bootstrap prompt is only sent for fresh sessions. Put stable setup, habits, and longer reusable guidance here. Frequent changes reduce the value of session reuse because new sessions must replay it.
+              </div>
               {adapterType === "claude_local" && (
                 <ClaudeLocalAdvancedFields {...adapterFieldProps} />
               )}

ui/src/components/InlineEditor.tsx

@@ -1,12 +1,11 @@
 import { useState, useRef, useEffect, useCallback } from "react";
 import { cn } from "../lib/utils";
-import { Button } from "@/components/ui/button";
-import { MarkdownBody } from "./MarkdownBody";
-import { MarkdownEditor, type MentionOption } from "./MarkdownEditor";
+import { MarkdownEditor, type MarkdownEditorRef, type MentionOption } from "./MarkdownEditor";
+import { useAutosaveIndicator } from "../hooks/useAutosaveIndicator";
 
 interface InlineEditorProps {
   value: string;
-  onSave: (value: string) => void;
+  onSave: (value: string) => void | Promise<unknown>;
   as?: "h1" | "h2" | "p" | "span";
   className?: string;
   placeholder?: string;
@@ -17,6 +16,8 @@ interface InlineEditorProps {
 
 /** Shared padding so display and edit modes occupy the exact same box. */
 const pad = "px-1 -mx-1";
+const markdownPad = "px-1";
+const AUTOSAVE_DEBOUNCE_MS = 900;
 
 export function InlineEditor({
   value,
@@ -29,12 +30,30 @@ export function InlineEditor({
   mentions,
 }: InlineEditorProps) {
   const [editing, setEditing] = useState(false);
+  const [multilineFocused, setMultilineFocused] = useState(false);
   const [draft, setDraft] = useState(value);
   const inputRef = useRef<HTMLTextAreaElement>(null);
+  const markdownRef = useRef<MarkdownEditorRef>(null);
+  const autosaveDebounceRef = useRef<ReturnType<typeof setTimeout> | null>(null);
+  const {
+    state: autosaveState,
+    markDirty,
+    reset,
+    runSave,
+  } = useAutosaveIndicator();
 
   useEffect(() => {
+    if (multiline && multilineFocused) return;
     setDraft(value);
-  }, [value]);
+  }, [value, multiline, multilineFocused]);
+
+  useEffect(() => {
+    return () => {
+      if (autosaveDebounceRef.current) {
+        clearTimeout(autosaveDebounceRef.current);
+      }
+    };
+  }, []);
 
   const autoSize = useCallback((el: HTMLTextAreaElement | null) => {
     if (!el) return;
@@ -52,58 +71,140 @@ export function InlineEditor({
     }
   }, [editing, autoSize]);
 
-  function commit() {
-    const trimmed = draft.trim();
+  useEffect(() => {
+    if (!editing || !multiline) return;
+    const frame = requestAnimationFrame(() => {
+      markdownRef.current?.focus();
+    });
+    return () => cancelAnimationFrame(frame);
+  }, [editing, multiline]);
+
+  const commit = useCallback(async (nextValue = draft) => {
+    const trimmed = nextValue.trim();
     if (trimmed && trimmed !== value) {
-      onSave(trimmed);
+      await Promise.resolve(onSave(trimmed));
     } else {
       setDraft(value);
     }
-    setEditing(false);
-  }
+    if (!multiline) {
+      setEditing(false);
+    }
+  }, [draft, multiline, onSave, value]);
 
   function handleKeyDown(e: React.KeyboardEvent) {
     if (e.key === "Enter" && !multiline) {
       e.preventDefault();
-      commit();
+      void commit();
     }
     if (e.key === "Escape") {
+      if (autosaveDebounceRef.current) {
+        clearTimeout(autosaveDebounceRef.current);
+      }
+      reset();
       setDraft(value);
-      setEditing(false);
+      if (multiline) {
+        setMultilineFocused(false);
+        if (document.activeElement instanceof HTMLElement) {
+          document.activeElement.blur();
+        }
+      } else {
+        setEditing(false);
+      }
     }
   }
 
-  if (editing) {
-    if (multiline) {
-      return (
-        <div className={cn("space-y-2", pad)}>
-          <MarkdownEditor
-            value={draft}
-            onChange={setDraft}
-            placeholder={placeholder}
-            contentClassName={className}
-            imageUploadHandler={imageUploadHandler}
-            mentions={mentions}
-            onSubmit={commit}
-          />
-          <div className="flex items-center justify-end gap-2">
-            <Button
-              variant="outline"
-              size="sm"
-              onClick={() => {
-                setDraft(value);
-                setEditing(false);
-              }}
-            >
-              Cancel
-            </Button>
-            <Button size="sm" onClick={commit}>
-              Save
-            </Button>
-          </div>
-        </div>
-      );
+  useEffect(() => {
+    if (!multiline) return;
+    if (!multilineFocused) return;
+    const trimmed = draft.trim();
+    if (!trimmed || trimmed === value) {
+      if (autosaveState !== "saved") {
+        reset();
+      }
+      return;
     }
+    markDirty();
+    if (autosaveDebounceRef.current) {
+      clearTimeout(autosaveDebounceRef.current);
+    }
+    autosaveDebounceRef.current = setTimeout(() => {
+      void runSave(() => commit(trimmed));
+    }, AUTOSAVE_DEBOUNCE_MS);
+
+    return () => {
+      if (autosaveDebounceRef.current) {
+        clearTimeout(autosaveDebounceRef.current);
+      }
+    };
+  }, [autosaveState, commit, draft, markDirty, multiline, multilineFocused, reset, runSave, value]);
+
+  if (multiline) {
+    return (
+      <div
+        className={cn(
+          markdownPad,
+          "rounded transition-colors",
+          multilineFocused ? "bg-transparent" : "hover:bg-accent/20",
+        )}
+        onFocusCapture={() => setMultilineFocused(true)}
+        onBlurCapture={(event) => {
+          if (event.currentTarget.contains(event.relatedTarget as Node | null)) return;
+          if (autosaveDebounceRef.current) {
+            clearTimeout(autosaveDebounceRef.current);
+          }
+          setMultilineFocused(false);
+          const trimmed = draft.trim();
+          if (!trimmed || trimmed === value) {
+            reset();
+            void commit();
+            return;
+          }
+          void runSave(() => commit());
+        }}
+        onKeyDown={handleKeyDown}
+      >
+        <MarkdownEditor
+          ref={markdownRef}
+          value={draft}
+          onChange={setDraft}
+          placeholder={placeholder}
+          bordered={false}
+          className="bg-transparent"
+          contentClassName={cn("paperclip-edit-in-place-content", className)}
+          imageUploadHandler={imageUploadHandler}
+          mentions={mentions}
+          onSubmit={() => {
+            const trimmed = draft.trim();
+            if (!trimmed || trimmed === value) {
+              reset();
+              void commit();
+              return;
+            }
+            void runSave(() => commit());
+          }}
+        />
+        <div className="flex min-h-4 items-center justify-end pr-1">
+          <span
+            className={cn(
+              "text-[11px] transition-opacity duration-150",
+              autosaveState === "error" ? "text-destructive" : "text-muted-foreground",
+              autosaveState === "idle" ? "opacity-0" : "opacity-100",
+            )}
+          >
+            {autosaveState === "saving"
+              ? "Autosaving..."
+              : autosaveState === "saved"
+                ? "Saved"
+                : autosaveState === "error"
+                  ? "Could not save"
+                  : "Idle"}
+          </span>
+        </div>
+      </div>
+    );
+  }
+
+  if (editing) {
 
     return (
       <textarea
@@ -114,7 +215,9 @@ export function InlineEditor({
           setDraft(e.target.value);
           autoSize(e.target);
         }}
-        onBlur={commit}
+        onBlur={() => {
+          void commit();
+        }}
         onKeyDown={handleKeyDown}
         className={cn(
           "w-full bg-transparent rounded outline-none resize-none overflow-hidden",
@@ -135,15 +238,11 @@ export function InlineEditor({
         "cursor-pointer rounded hover:bg-accent/50 transition-colors overflow-hidden",
         pad,
         !value && "text-muted-foreground italic",
-        className
+        className,
       )}
       onClick={() => setEditing(true)}
     >
-      {value && multiline ? (
-        <MarkdownBody>{value}</MarkdownBody>
-      ) : (
-        value || placeholder
-      )}
+      {value || placeholder}
     </DisplayTag>
   );
 }

ui/src/components/IssueDocumentsSection.tsx

@@ -0,0 +1,889 @@
+import { useCallback, useEffect, useMemo, useRef, useState, type ReactNode } from "react";
+import { useMutation, useQuery, useQueryClient } from "@tanstack/react-query";
+import type { Issue, IssueDocument } from "@paperclipai/shared";
+import { useLocation } from "@/lib/router";
+import { ApiError } from "../api/client";
+import { issuesApi } from "../api/issues";
+import { useAutosaveIndicator } from "../hooks/useAutosaveIndicator";
+import { queryKeys } from "../lib/queryKeys";
+import { cn, relativeTime } from "../lib/utils";
+import { MarkdownBody } from "./MarkdownBody";
+import { MarkdownEditor, type MentionOption } from "./MarkdownEditor";
+import { Button } from "@/components/ui/button";
+import { Input } from "@/components/ui/input";
+import {
+  DropdownMenu,
+  DropdownMenuContent,
+  DropdownMenuItem,
+  DropdownMenuSeparator,
+  DropdownMenuTrigger,
+} from "@/components/ui/dropdown-menu";
+import { Check, ChevronDown, ChevronRight, Copy, Download, FileText, MoreHorizontal, Plus, Trash2, X } from "lucide-react";
+
+type DraftState = {
+  key: string;
+  title: string;
+  body: string;
+  baseRevisionId: string | null;
+  isNew: boolean;
+};
+
+type DocumentConflictState = {
+  key: string;
+  serverDocument: IssueDocument;
+  localDraft: DraftState;
+  showRemote: boolean;
+};
+
+const DOCUMENT_AUTOSAVE_DEBOUNCE_MS = 900;
+const DOCUMENT_KEY_PATTERN = /^[a-z0-9][a-z0-9_-]*$/;
+const getFoldedDocumentsStorageKey = (issueId: string) => `paperclip:issue-document-folds:${issueId}`;
+
+function loadFoldedDocumentKeys(issueId: string) {
+  if (typeof window === "undefined") return [];
+  try {
+    const raw = window.localStorage.getItem(getFoldedDocumentsStorageKey(issueId));
+    if (!raw) return [];
+    const parsed = JSON.parse(raw);
+    return Array.isArray(parsed) ? parsed.filter((value): value is string => typeof value === "string") : [];
+  } catch {
+    return [];
+  }
+}
+
+function saveFoldedDocumentKeys(issueId: string, keys: string[]) {
+  if (typeof window === "undefined") return;
+  window.localStorage.setItem(getFoldedDocumentsStorageKey(issueId), JSON.stringify(keys));
+}
+
+function renderBody(body: string, className?: string) {
+  return <MarkdownBody className={className}>{body}</MarkdownBody>;
+}
+
+function isPlanKey(key: string) {
+  return key.trim().toLowerCase() === "plan";
+}
+
+function titlesMatchKey(title: string | null | undefined, key: string) {
+  return (title ?? "").trim().toLowerCase() === key.trim().toLowerCase();
+}
+
+function isDocumentConflictError(error: unknown) {
+  return error instanceof ApiError && error.status === 409;
+}
+
+function downloadDocumentFile(key: string, body: string) {
+  const blob = new Blob([body], { type: "text/markdown;charset=utf-8" });
+  const url = URL.createObjectURL(blob);
+  const anchor = document.createElement("a");
+  anchor.href = url;
+  anchor.download = `${key}.md`;
+  document.body.appendChild(anchor);
+  anchor.click();
+  anchor.remove();
+  URL.revokeObjectURL(url);
+}
+
+export function IssueDocumentsSection({
+  issue,
+  canDeleteDocuments,
+  mentions,
+  imageUploadHandler,
+  extraActions,
+}: {
+  issue: Issue;
+  canDeleteDocuments: boolean;
+  mentions?: MentionOption[];
+  imageUploadHandler?: (file: File) => Promise<string>;
+  extraActions?: ReactNode;
+}) {
+  const queryClient = useQueryClient();
+  const location = useLocation();
+  const [confirmDeleteKey, setConfirmDeleteKey] = useState<string | null>(null);
+  const [error, setError] = useState<string | null>(null);
+  const [draft, setDraft] = useState<DraftState | null>(null);
+  const [documentConflict, setDocumentConflict] = useState<DocumentConflictState | null>(null);
+  const [foldedDocumentKeys, setFoldedDocumentKeys] = useState<string[]>(() => loadFoldedDocumentKeys(issue.id));
+  const [autosaveDocumentKey, setAutosaveDocumentKey] = useState<string | null>(null);
+  const [copiedDocumentKey, setCopiedDocumentKey] = useState<string | null>(null);
+  const [highlightDocumentKey, setHighlightDocumentKey] = useState<string | null>(null);
+  const autosaveDebounceRef = useRef<ReturnType<typeof setTimeout> | null>(null);
+  const copiedDocumentTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
+  const hasScrolledToHashRef = useRef(false);
+  const {
+    state: autosaveState,
+    markDirty,
+    reset,
+    runSave,
+  } = useAutosaveIndicator();
+
+  const { data: documents } = useQuery({
+    queryKey: queryKeys.issues.documents(issue.id),
+    queryFn: () => issuesApi.listDocuments(issue.id),
+  });
+
+  const invalidateIssueDocuments = () => {
+    queryClient.invalidateQueries({ queryKey: queryKeys.issues.detail(issue.id) });
+    queryClient.invalidateQueries({ queryKey: queryKeys.issues.documents(issue.id) });
+  };
+
+  const upsertDocument = useMutation({
+    mutationFn: async (nextDraft: DraftState) =>
+      issuesApi.upsertDocument(issue.id, nextDraft.key, {
+        title: isPlanKey(nextDraft.key) ? null : nextDraft.title.trim() || null,
+        format: "markdown",
+        body: nextDraft.body,
+        baseRevisionId: nextDraft.baseRevisionId,
+      }),
+  });
+
+  const deleteDocument = useMutation({
+    mutationFn: (key: string) => issuesApi.deleteDocument(issue.id, key),
+    onSuccess: () => {
+      setError(null);
+      setConfirmDeleteKey(null);
+      invalidateIssueDocuments();
+    },
+    onError: (err) => {
+      setError(err instanceof Error ? err.message : "Failed to delete document");
+    },
+  });
+
+  const sortedDocuments = useMemo(() => {
+    return [...(documents ?? [])].sort((a, b) => {
+      if (a.key === "plan" && b.key !== "plan") return -1;
+      if (a.key !== "plan" && b.key === "plan") return 1;
+      return new Date(b.updatedAt).getTime() - new Date(a.updatedAt).getTime();
+    });
+  }, [documents]);
+
+  const hasRealPlan = sortedDocuments.some((doc) => doc.key === "plan");
+  const isEmpty = sortedDocuments.length === 0 && !issue.legacyPlanDocument;
+  const newDocumentKeyError =
+    draft?.isNew && draft.key.trim().length > 0 && !DOCUMENT_KEY_PATTERN.test(draft.key.trim())
+      ? "Use lowercase letters, numbers, -, or _, and start with a letter or number."
+      : null;
+
+  const resetAutosaveState = useCallback(() => {
+    setAutosaveDocumentKey(null);
+    reset();
+  }, [reset]);
+
+  const markDocumentDirty = useCallback((key: string) => {
+    setAutosaveDocumentKey(key);
+    markDirty();
+  }, [markDirty]);
+
+  const beginNewDocument = () => {
+    resetAutosaveState();
+    setDocumentConflict(null);
+    setDraft({
+      key: "",
+      title: "",
+      body: "",
+      baseRevisionId: null,
+      isNew: true,
+    });
+    setError(null);
+  };
+
+  const beginEdit = (key: string) => {
+    const doc = sortedDocuments.find((entry) => entry.key === key);
+    if (!doc) return;
+    const conflictedDraft = documentConflict?.key === key ? documentConflict.localDraft : null;
+    setFoldedDocumentKeys((current) => current.filter((entry) => entry !== key));
+    resetAutosaveState();
+    setDocumentConflict((current) => current?.key === key ? current : null);
+    setDraft({
+      key: conflictedDraft?.key ?? doc.key,
+      title: conflictedDraft?.title ?? doc.title ?? "",
+      body: conflictedDraft?.body ?? doc.body,
+      baseRevisionId: conflictedDraft?.baseRevisionId ?? doc.latestRevisionId,
+      isNew: false,
+    });
+    setError(null);
+  };
+
+  const cancelDraft = () => {
+    if (autosaveDebounceRef.current) {
+      clearTimeout(autosaveDebounceRef.current);
+    }
+    resetAutosaveState();
+    setDocumentConflict(null);
+    setDraft(null);
+    setError(null);
+  };
+
+  const commitDraft = useCallback(async (
+    currentDraft: DraftState | null,
+    options?: { clearAfterSave?: boolean; trackAutosave?: boolean; overrideConflict?: boolean },
+  ) => {
+    if (!currentDraft || upsertDocument.isPending) return false;
+    const normalizedKey = currentDraft.key.trim().toLowerCase();
+    const normalizedBody = currentDraft.body.trim();
+    const normalizedTitle = currentDraft.title.trim();
+    const activeConflict = documentConflict?.key === normalizedKey ? documentConflict : null;
+
+    if (activeConflict && !options?.overrideConflict) {
+      if (options?.trackAutosave) {
+        resetAutosaveState();
+      }
+      return false;
+    }
+
+    if (!normalizedKey || !normalizedBody) {
+      if (currentDraft.isNew) {
+        setError("Document key and body are required");
+      } else if (!normalizedBody) {
+        setError("Document body cannot be empty");
+      }
+      if (options?.trackAutosave) {
+        resetAutosaveState();
+      }
+      return false;
+    }
+
+    if (!DOCUMENT_KEY_PATTERN.test(normalizedKey)) {
+      setError("Document key must start with a letter or number and use only lowercase letters, numbers, -, or _.");
+      if (options?.trackAutosave) {
+        resetAutosaveState();
+      }
+      return false;
+    }
+
+    const existing = sortedDocuments.find((doc) => doc.key === normalizedKey);
+    if (
+      !currentDraft.isNew &&
+      existing &&
+      existing.body === currentDraft.body &&
+      (existing.title ?? "") === currentDraft.title
+    ) {
+      if (options?.clearAfterSave) {
+        setDraft((value) => (value?.key === normalizedKey ? null : value));
+      }
+      if (options?.trackAutosave) {
+        resetAutosaveState();
+      }
+      return true;
+    }
+
+    const save = async () => {
+      const saved = await upsertDocument.mutateAsync({
+        ...currentDraft,
+        key: normalizedKey,
+        title: isPlanKey(normalizedKey) ? "" : normalizedTitle,
+        body: currentDraft.body,
+        baseRevisionId: options?.overrideConflict
+          ? activeConflict?.serverDocument.latestRevisionId ?? currentDraft.baseRevisionId
+          : currentDraft.baseRevisionId,
+      });
+      setError(null);
+      setDocumentConflict((current) => current?.key === normalizedKey ? null : current);
+      setDraft((value) => {
+        if (!value || value.key !== normalizedKey) return value;
+        if (options?.clearAfterSave) return null;
+        return {
+          key: saved.key,
+          title: saved.title ?? "",
+          body: saved.body,
+          baseRevisionId: saved.latestRevisionId,
+          isNew: false,
+        };
+      });
+      invalidateIssueDocuments();
+    };
+
+    try {
+      if (options?.trackAutosave) {
+        setAutosaveDocumentKey(normalizedKey);
+        await runSave(save);
+      } else {
+        await save();
+      }
+      return true;
+    } catch (err) {
+      if (isDocumentConflictError(err)) {
+        try {
+          const latestDocument = await issuesApi.getDocument(issue.id, normalizedKey);
+          setDocumentConflict({
+            key: normalizedKey,
+            serverDocument: latestDocument,
+            localDraft: {
+              key: normalizedKey,
+              title: isPlanKey(normalizedKey) ? "" : normalizedTitle,
+              body: currentDraft.body,
+              baseRevisionId: currentDraft.baseRevisionId,
+              isNew: false,
+            },
+            showRemote: true,
+          });
+          setFoldedDocumentKeys((current) => current.filter((key) => key !== normalizedKey));
+          setError(null);
+          resetAutosaveState();
+          return false;
+        } catch {
+          setError("Document changed remotely and the latest version could not be loaded");
+          return false;
+        }
+      }
+      setError(err instanceof Error ? err.message : "Failed to save document");
+      return false;
+    }
+  }, [documentConflict, invalidateIssueDocuments, issue.id, resetAutosaveState, runSave, sortedDocuments, upsertDocument]);
+
+  const reloadDocumentFromServer = useCallback((key: string) => {
+    if (documentConflict?.key !== key) return;
+    const serverDocument = documentConflict.serverDocument;
+    setDraft({
+      key: serverDocument.key,
+      title: serverDocument.title ?? "",
+      body: serverDocument.body,
+      baseRevisionId: serverDocument.latestRevisionId,
+      isNew: false,
+    });
+    setDocumentConflict(null);
+    resetAutosaveState();
+    setError(null);
+  }, [documentConflict, resetAutosaveState]);
+
+  const overwriteDocumentFromDraft = useCallback(async (key: string) => {
+    if (documentConflict?.key !== key) return;
+    const sourceDraft =
+      draft && draft.key === key && !draft.isNew
+        ? draft
+        : documentConflict.localDraft;
+    await commitDraft(
+      {
+        ...sourceDraft,
+        baseRevisionId: documentConflict.serverDocument.latestRevisionId,
+      },
+      {
+        clearAfterSave: false,
+        trackAutosave: true,
+        overrideConflict: true,
+      },
+    );
+  }, [commitDraft, documentConflict, draft]);
+
+  const keepConflictedDraft = useCallback((key: string) => {
+    if (documentConflict?.key !== key) return;
+    setDraft(documentConflict.localDraft);
+    setDocumentConflict((current) =>
+      current?.key === key
+        ? { ...current, showRemote: false }
+        : current,
+    );
+    setError(null);
+  }, [documentConflict]);
+
+  const copyDocumentBody = useCallback(async (key: string, body: string) => {
+    try {
+      await navigator.clipboard.writeText(body);
+      setCopiedDocumentKey(key);
+      if (copiedDocumentTimerRef.current) {
+        clearTimeout(copiedDocumentTimerRef.current);
+      }
+      copiedDocumentTimerRef.current = setTimeout(() => {
+        setCopiedDocumentKey((current) => current === key ? null : current);
+      }, 1400);
+    } catch {
+      setError("Could not copy document");
+    }
+  }, []);
+
+  const handleDraftBlur = async (event: React.FocusEvent<HTMLDivElement>) => {
+    if (event.currentTarget.contains(event.relatedTarget as Node | null)) return;
+    if (autosaveDebounceRef.current) {
+      clearTimeout(autosaveDebounceRef.current);
+    }
+    await commitDraft(draft, { clearAfterSave: true, trackAutosave: true });
+  };
+
+  const handleDraftKeyDown = async (event: React.KeyboardEvent) => {
+    if (event.key === "Escape") {
+      event.preventDefault();
+      cancelDraft();
+      return;
+    }
+    if ((event.metaKey || event.ctrlKey) && event.key === "Enter") {
+      event.preventDefault();
+      if (autosaveDebounceRef.current) {
+        clearTimeout(autosaveDebounceRef.current);
+      }
+      await commitDraft(draft, { clearAfterSave: false, trackAutosave: true });
+    }
+  };
+
+  useEffect(() => {
+    setFoldedDocumentKeys(loadFoldedDocumentKeys(issue.id));
+  }, [issue.id]);
+
+  useEffect(() => {
+    hasScrolledToHashRef.current = false;
+  }, [issue.id, location.hash]);
+
+  useEffect(() => {
+    const validKeys = new Set(sortedDocuments.map((doc) => doc.key));
+    setFoldedDocumentKeys((current) => {
+      const next = current.filter((key) => validKeys.has(key));
+      if (next.length !== current.length) {
+        saveFoldedDocumentKeys(issue.id, next);
+      }
+      return next;
+    });
+  }, [issue.id, sortedDocuments]);
+
+  useEffect(() => {
+    saveFoldedDocumentKeys(issue.id, foldedDocumentKeys);
+  }, [foldedDocumentKeys, issue.id]);
+
+  useEffect(() => {
+    if (!documentConflict) return;
+    const latest = sortedDocuments.find((doc) => doc.key === documentConflict.key);
+    if (!latest || latest.latestRevisionId === documentConflict.serverDocument.latestRevisionId) return;
+    setDocumentConflict((current) =>
+      current?.key === latest.key
+        ? { ...current, serverDocument: latest }
+        : current,
+    );
+  }, [documentConflict, sortedDocuments]);
+
+  useEffect(() => {
+    const hash = location.hash;
+    if (!hash.startsWith("#document-")) return;
+    const documentKey = decodeURIComponent(hash.slice("#document-".length));
+    const targetExists = sortedDocuments.some((doc) => doc.key === documentKey)
+      || (documentKey === "plan" && Boolean(issue.legacyPlanDocument));
+    if (!targetExists || hasScrolledToHashRef.current) return;
+    setFoldedDocumentKeys((current) => current.filter((key) => key !== documentKey));
+    const element = document.getElementById(`document-${documentKey}`);
+    if (!element) return;
+    hasScrolledToHashRef.current = true;
+    setHighlightDocumentKey(documentKey);
+    element.scrollIntoView({ behavior: "smooth", block: "center" });
+    const timer = setTimeout(() => setHighlightDocumentKey((current) => current === documentKey ? null : current), 3000);
+    return () => clearTimeout(timer);
+  }, [issue.legacyPlanDocument, location.hash, sortedDocuments]);
+
+  useEffect(() => {
+    return () => {
+      if (autosaveDebounceRef.current) {
+        clearTimeout(autosaveDebounceRef.current);
+      }
+      if (copiedDocumentTimerRef.current) {
+        clearTimeout(copiedDocumentTimerRef.current);
+      }
+    };
+  }, []);
+
+  useEffect(() => {
+    if (!draft || draft.isNew) return;
+    if (documentConflict?.key === draft.key) return;
+    const existing = sortedDocuments.find((doc) => doc.key === draft.key);
+    if (!existing) return;
+    const hasChanges =
+      existing.body !== draft.body ||
+      (existing.title ?? "") !== draft.title;
+    if (!hasChanges) {
+      if (autosaveState !== "saved") {
+        resetAutosaveState();
+      }
+      return;
+    }
+    markDocumentDirty(draft.key);
+    if (autosaveDebounceRef.current) {
+      clearTimeout(autosaveDebounceRef.current);
+    }
+    autosaveDebounceRef.current = setTimeout(() => {
+      void commitDraft(draft, { clearAfterSave: false, trackAutosave: true });
+    }, DOCUMENT_AUTOSAVE_DEBOUNCE_MS);
+
+    return () => {
+      if (autosaveDebounceRef.current) {
+        clearTimeout(autosaveDebounceRef.current);
+      }
+    };
+  }, [autosaveState, commitDraft, documentConflict, draft, markDocumentDirty, resetAutosaveState, sortedDocuments]);
+
+  const documentBodyShellClassName = "mt-3 overflow-hidden rounded-md";
+  const documentBodyPaddingClassName = "";
+  const documentBodyContentClassName = "paperclip-edit-in-place-content min-h-[220px] text-[15px] leading-7";
+  const toggleFoldedDocument = (key: string) => {
+    setFoldedDocumentKeys((current) =>
+      current.includes(key)
+        ? current.filter((entry) => entry !== key)
+        : [...current, key],
+    );
+  };
+
+  return (
+    <div className="space-y-3">
+      {isEmpty && !draft?.isNew ? (
+        <div className="flex items-center justify-end gap-2">
+          {extraActions}
+          <Button variant="outline" size="sm" onClick={beginNewDocument}>
+            <Plus className="mr-1.5 h-3.5 w-3.5" />
+            New document
+          </Button>
+        </div>
+      ) : (
+        <div className="flex items-center justify-between gap-2">
+          <h3 className="text-sm font-medium text-muted-foreground">Documents</h3>
+          <div className="flex items-center gap-2">
+            {extraActions}
+            <Button variant="outline" size="sm" onClick={beginNewDocument}>
+              <Plus className="mr-1.5 h-3.5 w-3.5" />
+              New document
+            </Button>
+          </div>
+        </div>
+      )}
+
+      {error && <p className="text-xs text-destructive">{error}</p>}
+
+      {draft?.isNew && (
+        <div
+          className="space-y-3 rounded-lg border border-border bg-accent/10 p-3"
+          onBlurCapture={handleDraftBlur}
+          onKeyDown={handleDraftKeyDown}
+        >
+          <Input
+            autoFocus
+            value={draft.key}
+            onChange={(event) =>
+              setDraft((current) => current ? { ...current, key: event.target.value.toLowerCase() } : current)
+            }
+            placeholder="Document key"
+          />
+          {newDocumentKeyError && (
+            <p className="text-xs text-destructive">{newDocumentKeyError}</p>
+          )}
+          {!isPlanKey(draft.key) && (
+            <Input
+              value={draft.title}
+              onChange={(event) =>
+                setDraft((current) => current ? { ...current, title: event.target.value } : current)
+              }
+              placeholder="Optional title"
+            />
+          )}
+          <MarkdownEditor
+            value={draft.body}
+            onChange={(body) =>
+              setDraft((current) => current ? { ...current, body } : current)
+            }
+            placeholder="Markdown body"
+            bordered={false}
+            className="bg-transparent"
+            contentClassName="min-h-[220px] text-[15px] leading-7"
+            mentions={mentions}
+            imageUploadHandler={imageUploadHandler}
+            onSubmit={() => void commitDraft(draft, { clearAfterSave: false, trackAutosave: false })}
+          />
+          <div className="flex items-center justify-end gap-2">
+            <Button variant="outline" size="sm" onClick={cancelDraft}>
+              <X className="mr-1.5 h-3.5 w-3.5" />
+              Cancel
+            </Button>
+            <Button
+              size="sm"
+              onClick={() => void commitDraft(draft, { clearAfterSave: false, trackAutosave: false })}
+              disabled={upsertDocument.isPending}
+            >
+              {upsertDocument.isPending ? "Saving..." : "Create document"}
+            </Button>
+          </div>
+        </div>
+      )}
+
+      {!hasRealPlan && issue.legacyPlanDocument ? (
+        <div
+          id="document-plan"
+          className={cn(
+            "rounded-lg border border-amber-500/30 bg-amber-500/5 p-3 transition-colors duration-1000",
+            highlightDocumentKey === "plan" && "border-primary/50 bg-primary/5",
+          )}
+        >
+          <div className="mb-2 flex items-center gap-2">
+            <FileText className="h-4 w-4 text-amber-600" />
+            <span className="rounded-full border border-amber-500/30 px-2 py-0.5 font-mono text-[10px] uppercase tracking-[0.16em] text-amber-700 dark:text-amber-300">
+              PLAN
+            </span>
+          </div>
+          <div className={documentBodyPaddingClassName}>
+            {renderBody(issue.legacyPlanDocument.body, documentBodyContentClassName)}
+          </div>
+        </div>
+      ) : null}
+
+      <div className="space-y-3">
+        {sortedDocuments.map((doc) => {
+          const activeDraft = draft?.key === doc.key && !draft.isNew ? draft : null;
+          const activeConflict = documentConflict?.key === doc.key ? documentConflict : null;
+          const isFolded = foldedDocumentKeys.includes(doc.key);
+          const showTitle = !isPlanKey(doc.key) && !!doc.title?.trim() && !titlesMatchKey(doc.title, doc.key);
+
+          return (
+            <div
+              key={doc.id}
+              id={`document-${doc.key}`}
+              className={cn(
+                "rounded-lg border border-border p-3 transition-colors duration-1000",
+                highlightDocumentKey === doc.key && "border-primary/50 bg-primary/5",
+              )}
+            >
+              <div className="flex items-start justify-between gap-3">
+                <div className="min-w-0">
+                  <div className="flex items-center gap-2">
+                    <button
+                      type="button"
+                      className="inline-flex h-5 w-5 items-center justify-center rounded-sm text-muted-foreground transition-colors hover:bg-accent/60 hover:text-foreground"
+                      onClick={() => toggleFoldedDocument(doc.key)}
+                      aria-label={isFolded ? `Expand ${doc.key} document` : `Collapse ${doc.key} document`}
+                      aria-expanded={!isFolded}
+                    >
+                      {isFolded ? <ChevronRight className="h-3.5 w-3.5" /> : <ChevronDown className="h-3.5 w-3.5" />}
+                    </button>
+                    <span className="rounded-full border border-border px-2 py-0.5 font-mono text-[10px] uppercase tracking-[0.16em] text-muted-foreground">
+                      {doc.key}
+                    </span>
+                    <a
+                      href={`#document-${encodeURIComponent(doc.key)}`}
+                      className="text-[11px] text-muted-foreground transition-colors hover:text-foreground hover:underline"
+                    >
+                      rev {doc.latestRevisionNumber} • updated {relativeTime(doc.updatedAt)}
+                    </a>
+                  </div>
+                  {showTitle && <p className="mt-2 text-sm font-medium">{doc.title}</p>}
+                </div>
+                <div className="flex items-center gap-1">
+                  <Button
+                    variant="ghost"
+                    size="icon-xs"
+                    className={cn(
+                      "text-muted-foreground transition-colors",
+                      copiedDocumentKey === doc.key && "text-foreground",
+                    )}
+                    title={copiedDocumentKey === doc.key ? "Copied" : "Copy document"}
+                    onClick={() => void copyDocumentBody(doc.key, activeDraft?.body ?? doc.body)}
+                  >
+                    {copiedDocumentKey === doc.key ? (
+                      <Check className="h-3.5 w-3.5" />
+                    ) : (
+                      <Copy className="h-3.5 w-3.5" />
+                    )}
+                  </Button>
+                  <DropdownMenu>
+                    <DropdownMenuTrigger asChild>
+                      <Button
+                        variant="ghost"
+                        size="icon-xs"
+                        className="text-muted-foreground"
+                        title="Document actions"
+                      >
+                        <MoreHorizontal className="h-3.5 w-3.5" />
+                      </Button>
+                    </DropdownMenuTrigger>
+                    <DropdownMenuContent align="end">
+                      <DropdownMenuItem
+                        onClick={() => downloadDocumentFile(doc.key, activeDraft?.body ?? doc.body)}
+                      >
+                        <Download className="h-3.5 w-3.5" />
+                        Download document
+                      </DropdownMenuItem>
+                      {canDeleteDocuments ? <DropdownMenuSeparator /> : null}
+                      {canDeleteDocuments ? (
+                        <DropdownMenuItem
+                          variant="destructive"
+                          onClick={() => setConfirmDeleteKey(doc.key)}
+                        >
+                          <Trash2 className="h-3.5 w-3.5" />
+                          Delete document
+                        </DropdownMenuItem>
+                      ) : null}
+                    </DropdownMenuContent>
+                  </DropdownMenu>
+                </div>
+              </div>
+
+              {!isFolded ? (
+                <div
+                  className="mt-3 space-y-3"
+                  onFocusCapture={() => {
+                    if (!activeDraft) {
+                      beginEdit(doc.key);
+                    }
+                  }}
+                  onBlurCapture={async (event) => {
+                    if (activeDraft) {
+                      await handleDraftBlur(event);
+                    }
+                  }}
+                  onKeyDown={async (event) => {
+                    if (activeDraft) {
+                      await handleDraftKeyDown(event);
+                    }
+                  }}
+                >
+                  {activeConflict && (
+                    <div className="rounded-md border border-amber-500/30 bg-amber-500/5 px-3 py-3">
+                      <div className="flex flex-col gap-3 sm:flex-row sm:items-start sm:justify-between">
+                        <div className="space-y-1">
+                          <p className="text-sm font-medium text-amber-200">Out of date</p>
+                          <p className="text-xs text-muted-foreground">
+                            This document changed while you were editing. Your local draft is preserved and autosave is paused.
+                          </p>
+                        </div>
+                        <div className="flex flex-wrap items-center gap-2">
+                          <Button
+                            variant="outline"
+                            size="sm"
+                            onClick={() =>
+                              setDocumentConflict((current) =>
+                                current?.key === doc.key
+                                  ? { ...current, showRemote: !current.showRemote }
+                                  : current,
+                              )
+                            }
+                          >
+                            {activeConflict.showRemote ? "Hide remote" : "Review remote"}
+                          </Button>
+                          <Button
+                            variant="outline"
+                            size="sm"
+                            onClick={() => keepConflictedDraft(doc.key)}
+                          >
+                            Keep my draft
+                          </Button>
+                          <Button
+                            variant="outline"
+                            size="sm"
+                            onClick={() => reloadDocumentFromServer(doc.key)}
+                          >
+                            Reload remote
+                          </Button>
+                          <Button
+                            size="sm"
+                            onClick={() => void overwriteDocumentFromDraft(doc.key)}
+                            disabled={upsertDocument.isPending}
+                          >
+                            {upsertDocument.isPending ? "Saving..." : "Overwrite remote"}
+                          </Button>
+                        </div>
+                      </div>
+                      {activeConflict.showRemote && (
+                        <div className="mt-3 rounded-md border border-border/70 bg-background/60 p-3">
+                          <div className="mb-2 flex items-center gap-2 text-[11px] text-muted-foreground">
+                            <span>Remote revision {activeConflict.serverDocument.latestRevisionNumber}</span>
+                            <span>•</span>
+                            <span>updated {relativeTime(activeConflict.serverDocument.updatedAt)}</span>
+                          </div>
+                          {!isPlanKey(doc.key) && activeConflict.serverDocument.title ? (
+                            <p className="mb-2 text-sm font-medium">{activeConflict.serverDocument.title}</p>
+                          ) : null}
+                          {renderBody(activeConflict.serverDocument.body, "text-[14px] leading-7")}
+                        </div>
+                      )}
+                    </div>
+                  )}
+                  {activeDraft && !isPlanKey(doc.key) && (
+                    <Input
+                      value={activeDraft.title}
+                      onChange={(event) => {
+                        markDocumentDirty(doc.key);
+                        setDraft((current) => current ? { ...current, title: event.target.value } : current);
+                      }}
+                      placeholder="Optional title"
+                    />
+                  )}
+                  <div
+                    className={`${documentBodyShellClassName} ${documentBodyPaddingClassName} ${
+                      activeDraft ? "" : "hover:bg-accent/10"
+                    }`}
+                  >
+                    <MarkdownEditor
+                      value={activeDraft?.body ?? doc.body}
+                      onChange={(body) => {
+                        markDocumentDirty(doc.key);
+                        setDraft((current) => {
+                          if (current && current.key === doc.key && !current.isNew) {
+                            return { ...current, body };
+                          }
+                          return {
+                            key: doc.key,
+                            title: doc.title ?? "",
+                            body,
+                            baseRevisionId: doc.latestRevisionId,
+                            isNew: false,
+                          };
+                        });
+                      }}
+                      placeholder="Markdown body"
+                      bordered={false}
+                      className="bg-transparent"
+                      contentClassName={documentBodyContentClassName}
+                      mentions={mentions}
+                      imageUploadHandler={imageUploadHandler}
+                      onSubmit={() => void commitDraft(activeDraft ?? draft, { clearAfterSave: false, trackAutosave: true })}
+                    />
+                  </div>
+                  <div className="flex min-h-4 items-center justify-end px-1">
+                    <span
+                      className={`text-[11px] transition-opacity duration-150 ${
+                        activeConflict
+                          ? "text-amber-300"
+                          : autosaveState === "error"
+                            ? "text-destructive"
+                            : "text-muted-foreground"
+                      } ${activeDraft ? "opacity-100" : "opacity-0"}`}
+                    >
+                      {activeDraft
+                        ? activeConflict
+                          ? "Out of date"
+                          : autosaveDocumentKey === doc.key
+                            ? autosaveState === "saving"
+                              ? "Autosaving..."
+                              : autosaveState === "saved"
+                                ? "Saved"
+                                : autosaveState === "error"
+                                  ? "Could not save"
+                                  : ""
+                            : ""
+                        : ""}
+                    </span>
+                  </div>
+                </div>
+              ) : null}
+
+              {confirmDeleteKey === doc.key && (
+                <div className="mt-3 flex items-center justify-between gap-3 rounded-md border border-destructive/20 bg-destructive/5 px-4 py-3">
+                  <p className="text-sm text-destructive font-medium">
+                    Delete this document? This cannot be undone.
+                  </p>
+                  <div className="flex items-center gap-2 shrink-0">
+                    <Button
+                      variant="ghost"
+                      size="sm"
+                      onClick={() => setConfirmDeleteKey(null)}
+                      disabled={deleteDocument.isPending}
+                    >
+                      Cancel
+                    </Button>
+                    <Button
+                      variant="destructive"
+                      size="sm"
+                      onClick={() => deleteDocument.mutate(doc.key)}
+                      disabled={deleteDocument.isPending}
+                    >
+                      {deleteDocument.isPending ? "Deleting..." : "Delete"}
+                    </Button>
+                  </div>
+                </div>
+              )}
+            </div>
+          );
+        })}
+      </div>
+    </div>
+  );
+}

ui/src/components/NewIssueDialog.tsx

@@ -1,4 +1,4 @@
-import { useState, useEffect, useRef, useCallback, useMemo, type ChangeEvent } from "react";
+import { useState, useEffect, useRef, useCallback, useMemo, type ChangeEvent, type DragEvent } from "react";
 import { useQuery, useMutation, useQueryClient } from "@tanstack/react-query";
 import { useDialog } from "../context/DialogContext";
 import { useCompany } from "../context/CompanyContext";
@@ -10,6 +10,7 @@ import { assetsApi } from "../api/assets";
 import { queryKeys } from "../lib/queryKeys";
 import { useProjectOrder } from "../hooks/useProjectOrder";
 import { getRecentAssigneeIds, sortAgentsByRecency, trackRecentAssignee } from "../lib/recent-assignees";
+import { useToast } from "../context/ToastContext";
 import {
   assigneeValueFromSelection,
   currentUserAssigneeOption,
@@ -39,7 +40,9 @@ import {
   Tag,
   Calendar,
   Paperclip,
+  FileText,
   Loader2,
+  X,
 } from "lucide-react";
 import { cn } from "../lib/utils";
 import { extractProviderIdWithFallback } from "../lib/model-utils";
@@ -77,7 +80,16 @@ interface IssueDraft {
   useIsolatedExecutionWorkspace: boolean;
 }
 
+type StagedIssueFile = {
+  id: string;
+  file: File;
+  kind: "document" | "attachment";
+  documentKey?: string;
+  title?: string | null;
+};
+
 const ISSUE_OVERRIDE_ADAPTER_TYPES = new Set(["claude_local", "codex_local", "opencode_local"]);
+const STAGED_FILE_ACCEPT = "image/*,application/pdf,text/plain,text/markdown,application/json,text/csv,text/html,.md,.markdown";
 
 const ISSUE_THINKING_EFFORT_OPTIONS = {
   claude_local: [
@@ -156,6 +168,59 @@ function clearDraft() {
   localStorage.removeItem(DRAFT_KEY);
 }
 
+function isTextDocumentFile(file: File) {
+  const name = file.name.toLowerCase();
+  return (
+    name.endsWith(".md") ||
+    name.endsWith(".markdown") ||
+    name.endsWith(".txt") ||
+    file.type === "text/markdown" ||
+    file.type === "text/plain"
+  );
+}
+
+function fileBaseName(filename: string) {
+  return filename.replace(/\.[^.]+$/, "");
+}
+
+function slugifyDocumentKey(input: string) {
+  const slug = input
+    .trim()
+    .toLowerCase()
+    .replace(/[^a-z0-9]+/g, "-")
+    .replace(/^-+|-+$/g, "");
+  return slug || "document";
+}
+
+function titleizeFilename(input: string) {
+  return input
+    .split(/[-_ ]+/g)
+    .filter(Boolean)
+    .map((part) => part.charAt(0).toUpperCase() + part.slice(1))
+    .join(" ");
+}
+
+function createUniqueDocumentKey(baseKey: string, stagedFiles: StagedIssueFile[]) {
+  const existingKeys = new Set(
+    stagedFiles
+      .filter((file) => file.kind === "document")
+      .map((file) => file.documentKey)
+      .filter((key): key is string => Boolean(key)),
+  );
+  if (!existingKeys.has(baseKey)) return baseKey;
+  let suffix = 2;
+  while (existingKeys.has(`${baseKey}-${suffix}`)) {
+    suffix += 1;
+  }
+  return `${baseKey}-${suffix}`;
+}
+
+function formatFileSize(file: File) {
+  if (file.size < 1024) return `${file.size} B`;
+  if (file.size < 1024 * 1024) return `${(file.size / 1024).toFixed(1)} KB`;
+  return `${(file.size / (1024 * 1024)).toFixed(1)} MB`;
+}
+
 const statuses = [
   { value: "backlog", label: "Backlog", color: issueStatusText.backlog ?? issueStatusTextDefault },
   { value: "todo", label: "Todo", color: issueStatusText.todo ?? issueStatusTextDefault },
@@ -175,6 +240,7 @@ export function NewIssueDialog() {
   const { newIssueOpen, newIssueDefaults, closeNewIssue } = useDialog();
   const { companies, selectedCompanyId, selectedCompany } = useCompany();
   const queryClient = useQueryClient();
+  const { pushToast } = useToast();
   const [title, setTitle] = useState("");
   const [description, setDescription] = useState("");
   const [status, setStatus] = useState("todo");
@@ -188,6 +254,8 @@ export function NewIssueDialog() {
   const [useIsolatedExecutionWorkspace, setUseIsolatedExecutionWorkspace] = useState(false);
   const [expanded, setExpanded] = useState(false);
   const [dialogCompanyId, setDialogCompanyId] = useState<string | null>(null);
+  const [stagedFiles, setStagedFiles] = useState<StagedIssueFile[]>([]);
+  const [isFileDragOver, setIsFileDragOver] = useState(false);
   const draftTimer = useRef<ReturnType<typeof setTimeout> | null>(null);
   const executionWorkspaceDefaultProjectId = useRef<string | null>(null);
 
@@ -200,7 +268,7 @@ export function NewIssueDialog() {
   const [moreOpen, setMoreOpen] = useState(false);
   const [companyOpen, setCompanyOpen] = useState(false);
   const descriptionEditorRef = useRef<MarkdownEditorRef>(null);
-  const attachInputRef = useRef<HTMLInputElement | null>(null);
+  const stageFileInputRef = useRef<HTMLInputElement | null>(null);
   const assigneeSelectorRef = useRef<HTMLButtonElement | null>(null);
   const projectSelectorRef = useRef<HTMLButtonElement | null>(null);
 
@@ -268,11 +336,49 @@ export function NewIssueDialog() {
   });
 
   const createIssue = useMutation({
-    mutationFn: ({ companyId, ...data }: { companyId: string } & Record<string, unknown>) =>
-      issuesApi.create(companyId, data),
-    onSuccess: () => {
-      queryClient.invalidateQueries({ queryKey: queryKeys.issues.list(effectiveCompanyId!) });
+    mutationFn: async ({
+      companyId,
+      stagedFiles: pendingStagedFiles,
+      ...data
+    }: { companyId: string; stagedFiles: StagedIssueFile[] } & Record<string, unknown>) => {
+      const issue = await issuesApi.create(companyId, data);
+      const failures: string[] = [];
+
+      for (const stagedFile of pendingStagedFiles) {
+        try {
+          if (stagedFile.kind === "document") {
+            const body = await stagedFile.file.text();
+            await issuesApi.upsertDocument(issue.id, stagedFile.documentKey ?? "document", {
+              title: stagedFile.documentKey === "plan" ? null : stagedFile.title ?? null,
+              format: "markdown",
+              body,
+              baseRevisionId: null,
+            });
+          } else {
+            await issuesApi.uploadAttachment(companyId, issue.id, stagedFile.file);
+          }
+        } catch {
+          failures.push(stagedFile.file.name);
+        }
+      }
+
+      return { issue, companyId, failures };
+    },
+    onSuccess: ({ issue, companyId, failures }) => {
+      queryClient.invalidateQueries({ queryKey: queryKeys.issues.list(companyId) });
       if (draftTimer.current) clearTimeout(draftTimer.current);
+      if (failures.length > 0) {
+        const prefix = (companies.find((company) => company.id === companyId)?.issuePrefix ?? "").trim();
+        const issueRef = issue.identifier ?? issue.id;
+        pushToast({
+          title: `Created ${issueRef} with upload warnings`,
+          body: `${failures.length} staged ${failures.length === 1 ? "file" : "files"} could not be added.`,
+          tone: "warn",
+          action: prefix
+            ? { label: `Open ${issueRef}`, href: `/${prefix}/issues/${issueRef}` }
+            : undefined,
+        });
+      }
       clearDraft();
       reset();
       closeNewIssue();
@@ -413,6 +519,8 @@ export function NewIssueDialog() {
     setUseIsolatedExecutionWorkspace(false);
     setExpanded(false);
     setDialogCompanyId(null);
+    setStagedFiles([]);
+    setIsFileDragOver(false);
     setCompanyOpen(false);
     executionWorkspaceDefaultProjectId.current = null;
   }
@@ -453,6 +561,7 @@ export function NewIssueDialog() {
       : null;
     createIssue.mutate({
       companyId: effectiveCompanyId,
+      stagedFiles,
       title: title.trim(),
       description: description.trim() || undefined,
       status,
@@ -472,22 +581,70 @@ export function NewIssueDialog() {
     }
   }
 
-  async function handleAttachImage(evt: ChangeEvent<HTMLInputElement>) {
-    const file = evt.target.files?.[0];
-    if (!file) return;
-    try {
-      const asset = await uploadDescriptionImage.mutateAsync(file);
-      const name = file.name || "image";
-      setDescription((prev) => {
-        const suffix = `![${name}](${asset.contentPath})`;
-        return prev ? `${prev}\n\n${suffix}` : suffix;
-      });
-    } finally {
-      if (attachInputRef.current) attachInputRef.current.value = "";
+  function stageFiles(files: File[]) {
+    if (files.length === 0) return;
+    setStagedFiles((current) => {
+      const next = [...current];
+      for (const file of files) {
+        if (isTextDocumentFile(file)) {
+          const baseName = fileBaseName(file.name);
+          const documentKey = createUniqueDocumentKey(slugifyDocumentKey(baseName), next);
+          next.push({
+            id: `${file.name}:${file.size}:${file.lastModified}:${documentKey}`,
+            file,
+            kind: "document",
+            documentKey,
+            title: titleizeFilename(baseName),
+          });
+          continue;
+        }
+        next.push({
+          id: `${file.name}:${file.size}:${file.lastModified}`,
+          file,
+          kind: "attachment",
+        });
+      }
+      return next;
+    });
+  }
+
+  function handleStageFilesPicked(evt: ChangeEvent<HTMLInputElement>) {
+    stageFiles(Array.from(evt.target.files ?? []));
+    if (stageFileInputRef.current) {
+      stageFileInputRef.current.value = "";
     }
   }
 
-  const hasDraft = title.trim().length > 0 || description.trim().length > 0;
+  function handleFileDragEnter(evt: DragEvent<HTMLDivElement>) {
+    if (!evt.dataTransfer.types.includes("Files")) return;
+    evt.preventDefault();
+    setIsFileDragOver(true);
+  }
+
+  function handleFileDragOver(evt: DragEvent<HTMLDivElement>) {
+    if (!evt.dataTransfer.types.includes("Files")) return;
+    evt.preventDefault();
+    evt.dataTransfer.dropEffect = "copy";
+    setIsFileDragOver(true);
+  }
+
+  function handleFileDragLeave(evt: DragEvent<HTMLDivElement>) {
+    if (evt.currentTarget.contains(evt.relatedTarget as Node | null)) return;
+    setIsFileDragOver(false);
+  }
+
+  function handleFileDrop(evt: DragEvent<HTMLDivElement>) {
+    if (!evt.dataTransfer.files.length) return;
+    evt.preventDefault();
+    setIsFileDragOver(false);
+    stageFiles(Array.from(evt.dataTransfer.files));
+  }
+
+  function removeStagedFile(id: string) {
+    setStagedFiles((current) => current.filter((file) => file.id !== id));
+  }
+
+  const hasDraft = title.trim().length > 0 || description.trim().length > 0 || stagedFiles.length > 0;
   const currentStatus = statuses.find((s) => s.value === status) ?? statuses[1]!;
   const currentPriority = priorities.find((p) => p.value === priority);
   const currentAssignee = selectedAssigneeAgentId
@@ -541,6 +698,8 @@ export function NewIssueDialog() {
   const canDiscardDraft = hasDraft || hasSavedDraft;
   const createIssueErrorMessage =
     createIssue.error instanceof Error ? createIssue.error.message : "Failed to create issue. Try again.";
+  const stagedDocuments = stagedFiles.filter((file) => file.kind === "document");
+  const stagedAttachments = stagedFiles.filter((file) => file.kind === "attachment");
 
   const handleProjectChange = useCallback((nextProjectId: string) => {
     setProjectId(nextProjectId);
@@ -938,20 +1097,103 @@ export function NewIssueDialog() {
         )}
 
         {/* Description */}
-        <div className={cn("px-4 pb-2 overflow-y-auto min-h-0 border-t border-border/60 pt-3", expanded ? "flex-1" : "")}>
-          <MarkdownEditor
-            ref={descriptionEditorRef}
-            value={description}
-            onChange={setDescription}
-            placeholder="Add description..."
-            bordered={false}
-            mentions={mentionOptions}
-            contentClassName={cn("text-sm text-muted-foreground pb-12", expanded ? "min-h-[220px]" : "min-h-[120px]")}
-            imageUploadHandler={async (file) => {
-              const asset = await uploadDescriptionImage.mutateAsync(file);
-              return asset.contentPath;
-            }}
-          />
+        <div
+          className={cn("px-4 pb-2 overflow-y-auto min-h-0 border-t border-border/60 pt-3", expanded ? "flex-1" : "")}
+          onDragEnter={handleFileDragEnter}
+          onDragOver={handleFileDragOver}
+          onDragLeave={handleFileDragLeave}
+          onDrop={handleFileDrop}
+        >
+          <div
+            className={cn(
+              "rounded-md transition-colors",
+              isFileDragOver && "bg-accent/20",
+            )}
+          >
+            <MarkdownEditor
+              ref={descriptionEditorRef}
+              value={description}
+              onChange={setDescription}
+              placeholder="Add description..."
+              bordered={false}
+              mentions={mentionOptions}
+              contentClassName={cn("text-sm text-muted-foreground pb-12", expanded ? "min-h-[220px]" : "min-h-[120px]")}
+              imageUploadHandler={async (file) => {
+                const asset = await uploadDescriptionImage.mutateAsync(file);
+                return asset.contentPath;
+              }}
+            />
+          </div>
+          {stagedFiles.length > 0 ? (
+            <div className="mt-4 space-y-3 rounded-lg border border-border/70 p-3">
+              {stagedDocuments.length > 0 ? (
+                <div className="space-y-2">
+                  <div className="text-xs font-medium text-muted-foreground">Documents</div>
+                  <div className="space-y-2">
+                    {stagedDocuments.map((file) => (
+                      <div key={file.id} className="flex items-start justify-between gap-3 rounded-md border border-border/70 px-3 py-2">
+                        <div className="min-w-0">
+                          <div className="flex items-center gap-2">
+                            <span className="rounded-full border border-border px-2 py-0.5 font-mono text-[10px] uppercase tracking-[0.16em] text-muted-foreground">
+                              {file.documentKey}
+                            </span>
+                            <span className="truncate text-sm">{file.file.name}</span>
+                          </div>
+                          <div className="mt-1 flex items-center gap-2 text-[11px] text-muted-foreground">
+                            <FileText className="h-3.5 w-3.5" />
+                            <span>{file.title || file.file.name}</span>
+                            <span>•</span>
+                            <span>{formatFileSize(file.file)}</span>
+                          </div>
+                        </div>
+                        <Button
+                          variant="ghost"
+                          size="icon-xs"
+                          className="shrink-0 text-muted-foreground"
+                          onClick={() => removeStagedFile(file.id)}
+                          disabled={createIssue.isPending}
+                          title="Remove document"
+                        >
+                          <X className="h-3.5 w-3.5" />
+                        </Button>
+                      </div>
+                    ))}
+                  </div>
+                </div>
+              ) : null}
+
+              {stagedAttachments.length > 0 ? (
+                <div className="space-y-2">
+                  <div className="text-xs font-medium text-muted-foreground">Attachments</div>
+                  <div className="space-y-2">
+                    {stagedAttachments.map((file) => (
+                      <div key={file.id} className="flex items-start justify-between gap-3 rounded-md border border-border/70 px-3 py-2">
+                        <div className="min-w-0">
+                          <div className="flex items-center gap-2">
+                            <Paperclip className="h-3.5 w-3.5 shrink-0 text-muted-foreground" />
+                            <span className="truncate text-sm">{file.file.name}</span>
+                          </div>
+                          <div className="mt-1 text-[11px] text-muted-foreground">
+                            {file.file.type || "application/octet-stream"} • {formatFileSize(file.file)}
+                          </div>
+                        </div>
+                        <Button
+                          variant="ghost"
+                          size="icon-xs"
+                          className="shrink-0 text-muted-foreground"
+                          onClick={() => removeStagedFile(file.id)}
+                          disabled={createIssue.isPending}
+                          title="Remove attachment"
+                        >
+                          <X className="h-3.5 w-3.5" />
+                        </Button>
+                      </div>
+                    ))}
+                  </div>
+                </div>
+              ) : null}
+            </div>
+          ) : null}
         </div>
 
         {/* Property chips bar */}
@@ -1021,21 +1263,21 @@ export function NewIssueDialog() {
             Labels
           </button>
 
-          {/* Attach image chip */}
           <input
-            ref={attachInputRef}
+            ref={stageFileInputRef}
             type="file"
-            accept="image/png,image/jpeg,image/webp,image/gif"
+            accept={STAGED_FILE_ACCEPT}
             className="hidden"
-            onChange={handleAttachImage}
+            onChange={handleStageFilesPicked}
+            multiple
           />
           <button
             className="inline-flex items-center gap-1.5 rounded-md border border-border px-2 py-1 text-xs hover:bg-accent/50 transition-colors text-muted-foreground"
-            onClick={() => attachInputRef.current?.click()}
-            disabled={uploadDescriptionImage.isPending}
+            onClick={() => stageFileInputRef.current?.click()}
+            disabled={createIssue.isPending}
           >
             <Paperclip className="h-3 w-3" />
-            {uploadDescriptionImage.isPending ? "Uploading..." : "Image"}
+            Upload
           </button>
 
           {/* More (dates) */}

ui/src/components/agent-config-primitives.tsx

@@ -26,7 +26,7 @@ export const help: Record<string, string> = {
   capabilities: "Describes what this agent can do. Shown in the org chart and used for task routing.",
   adapterType: "How this agent runs: local CLI (Claude/Codex/OpenCode), OpenClaw Gateway, spawned process, or generic HTTP webhook.",
   cwd: "Default working directory fallback for local adapters. Use an absolute path on the machine running Paperclip.",
-  promptTemplate: "The prompt sent to the agent on each heartbeat. Supports {{ agent.id }}, {{ agent.name }}, {{ agent.role }} variables.",
+  promptTemplate: "Sent on every heartbeat. Keep this small and dynamic. Use it for current-task framing, not large static instructions. Supports {{ agent.id }}, {{ agent.name }}, {{ agent.role }} and other template variables.",
   model: "Override the default model used by the adapter.",
   thinkingEffort: "Control model reasoning depth. Supported values vary by adapter/model.",
   chrome: "Enable Claude's Chrome integration by passing --chrome.",
@@ -44,7 +44,7 @@ export const help: Record<string, string> = {
   args: "Command-line arguments, comma-separated.",
   extraArgs: "Extra CLI arguments for local adapters, comma-separated.",
   envVars: "Environment variables injected into the adapter process. Use plain values or secret references.",
-  bootstrapPrompt: "Optional prompt prepended on the first run to bootstrap the agent's environment or habits.",
+  bootstrapPrompt: "Only sent when Paperclip starts a fresh session. Use this for stable setup guidance that should not be repeated on every heartbeat.",
   payloadTemplateJson: "Optional JSON merged into remote adapter request payloads before Paperclip adds its standard wake and workspace fields.",
   webhookUrl: "The URL that receives POST requests when the agent is invoked.",
   heartbeatInterval: "Run this agent automatically on a timer. Useful for periodic tasks like checking for new work.",

ui/src/context/LiveUpdatesProvider.tsx

@@ -369,6 +369,9 @@ function invalidateActivityQueries(
         queryClient.invalidateQueries({ queryKey: queryKeys.issues.comments(ref) });
         queryClient.invalidateQueries({ queryKey: queryKeys.issues.activity(ref) });
         queryClient.invalidateQueries({ queryKey: queryKeys.issues.runs(ref) });
+        queryClient.invalidateQueries({ queryKey: queryKeys.issues.documents(ref) });
+        queryClient.invalidateQueries({ queryKey: queryKeys.issues.attachments(ref) });
+        queryClient.invalidateQueries({ queryKey: queryKeys.issues.approvals(ref) });
         queryClient.invalidateQueries({ queryKey: queryKeys.issues.liveRuns(ref) });
         queryClient.invalidateQueries({ queryKey: queryKeys.issues.activeRun(ref) });
       }

ui/src/hooks/useAutosaveIndicator.ts

@@ -0,0 +1,72 @@
+import { useCallback, useEffect, useRef, useState } from "react";
+
+export type AutosaveState = "idle" | "saving" | "saved" | "error";
+
+const SAVING_DELAY_MS = 250;
+const SAVED_LINGER_MS = 1600;
+
+export function useAutosaveIndicator() {
+  const [state, setState] = useState<AutosaveState>("idle");
+  const saveIdRef = useRef(0);
+  const savingTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
+  const clearSavedTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
+
+  const clearTimers = useCallback(() => {
+    if (savingTimerRef.current) {
+      clearTimeout(savingTimerRef.current);
+      savingTimerRef.current = null;
+    }
+    if (clearSavedTimerRef.current) {
+      clearTimeout(clearSavedTimerRef.current);
+      clearSavedTimerRef.current = null;
+    }
+  }, []);
+
+  useEffect(() => clearTimers, [clearTimers]);
+
+  const reset = useCallback(() => {
+    saveIdRef.current += 1;
+    clearTimers();
+    setState("idle");
+  }, [clearTimers]);
+
+  const markDirty = useCallback(() => {
+    clearTimers();
+    setState("idle");
+  }, [clearTimers]);
+
+  const runSave = useCallback(async (save: () => Promise<void>) => {
+    const saveId = saveIdRef.current + 1;
+    saveIdRef.current = saveId;
+    clearTimers();
+    savingTimerRef.current = setTimeout(() => {
+      if (saveIdRef.current === saveId) {
+        setState("saving");
+      }
+    }, SAVING_DELAY_MS);
+
+    try {
+      await save();
+      if (saveIdRef.current !== saveId) return;
+      clearTimers();
+      setState("saved");
+      clearSavedTimerRef.current = setTimeout(() => {
+        if (saveIdRef.current === saveId) {
+          setState("idle");
+        }
+      }, SAVED_LINGER_MS);
+    } catch (error) {
+      if (saveIdRef.current !== saveId) throw error;
+      clearTimers();
+      setState("error");
+      throw error;
+    }
+  }, [clearTimers]);
+
+  return {
+    state,
+    markDirty,
+    reset,
+    runSave,
+  };
+}

ui/src/index.css

@@ -307,6 +307,11 @@
   color: inherit;
 }
 
+.paperclip-edit-in-place-content {
+  font-size: 0.9375rem;
+  line-height: 1.75rem;
+}
+
 .paperclip-mdxeditor-content > *:first-child {
   margin-top: 0;
 }
@@ -317,11 +322,11 @@
 
 .paperclip-mdxeditor-content p {
   margin: 0;
-  line-height: 1.4;
+  line-height: inherit;
 }
 
 .paperclip-mdxeditor-content p + p {
-  margin-top: 0.6rem;
+  margin-top: 1.1em;
 }
 
 .paperclip-mdxeditor-content a.paperclip-project-mention-chip {
@@ -342,8 +347,8 @@
 
 .paperclip-mdxeditor-content ul,
 .paperclip-mdxeditor-content ol {
-  margin: 0.35rem 0;
-  padding-left: 1.1rem;
+  margin: 1.1em 0;
+  padding-left: 1.6em;
 }
 
 .paperclip-mdxeditor-content ul {
@@ -356,32 +361,46 @@
 
 .paperclip-mdxeditor-content li {
   display: list-item;
-  margin: 0.15rem 0;
-  line-height: 1.4;
+  margin: 0.3em 0;
+  line-height: inherit;
 }
 
 .paperclip-mdxeditor-content li::marker {
   color: var(--muted-foreground);
 }
 
-.paperclip-mdxeditor-content h1,
-.paperclip-mdxeditor-content h2,
-.paperclip-mdxeditor-content h3 {
-  margin: 0.4rem 0 0.25rem;
+.paperclip-mdxeditor-content h1 {
+  margin: 0 0 0.9em;
+  font-size: 1.75em;
+  font-weight: 700;
+  line-height: 1.2;
+}
+
+.paperclip-mdxeditor-content h2 {
+  margin: 0 0 0.85em;
+  font-size: 1.35em;
+  font-weight: 700;
   line-height: 1.3;
 }
 
+.paperclip-mdxeditor-content h3 {
+  margin: 0 0 0.8em;
+  font-size: 1.15em;
+  font-weight: 600;
+  line-height: 1.35;
+}
+
 .paperclip-mdxeditor-content img {
   max-height: 18rem;
   border-radius: calc(var(--radius) - 2px);
 }
 
 .paperclip-mdxeditor-content blockquote {
-  margin: 0.45rem 0;
-  padding-left: 0.7rem;
-  border-left: 2px solid var(--border);
+  margin: 1.2em 0;
+  padding-left: 1em;
+  border-left: 3px solid var(--border);
   color: var(--muted-foreground);
-  line-height: 1.4;
+  line-height: inherit;
 }
 
 .paperclip-mdxeditor-content code {

ui/src/lib/queryKeys.ts

@@ -27,6 +27,8 @@ export const queryKeys = {
     detail: (id: string) => ["issues", "detail", id] as const,
     comments: (issueId: string) => ["issues", "comments", issueId] as const,
     attachments: (issueId: string) => ["issues", "attachments", issueId] as const,
+    documents: (issueId: string) => ["issues", "documents", issueId] as const,
+    documentRevisions: (issueId: string, key: string) => ["issues", "document-revisions", issueId, key] as const,
     activity: (issueId: string) => ["issues", "activity", issueId] as const,
     runs: (issueId: string) => ["issues", "runs", issueId] as const,
     approvals: (issueId: string) => ["issues", "approvals", issueId] as const,

ui/src/pages/IssueDetail.tsx

@@ -1,4 +1,4 @@
-import { useEffect, useMemo, useRef, useState, type ChangeEvent } from "react";
+import { useEffect, useMemo, useRef, useState, type ChangeEvent, type DragEvent } from "react";
 import { Link, useLocation, useNavigate, useParams } from "@/lib/router";
 import { useQuery, useMutation, useQueryClient } from "@tanstack/react-query";
 import { issuesApi } from "../api/issues";
@@ -16,6 +16,7 @@ import { useProjectOrder } from "../hooks/useProjectOrder";
 import { relativeTime, cn, formatTokens } from "../lib/utils";
 import { InlineEditor } from "../components/InlineEditor";
 import { CommentThread } from "../components/CommentThread";
+import { IssueDocumentsSection } from "../components/IssueDocumentsSection";
 import { IssueProperties } from "../components/IssueProperties";
 import { LiveRunWidget } from "../components/LiveRunWidget";
 import type { MentionOption } from "../components/MarkdownEditor";
@@ -62,6 +63,9 @@ const ACTION_LABELS: Record<string, string> = {
   "issue.comment_added": "added a comment",
   "issue.attachment_added": "added an attachment",
   "issue.attachment_removed": "removed an attachment",
+  "issue.document_created": "created a document",
+  "issue.document_updated": "updated a document",
+  "issue.document_deleted": "deleted a document",
   "issue.deleted": "deleted the issue",
   "agent.created": "created an agent",
   "agent.updated": "updated the agent",
@@ -99,6 +103,36 @@ function truncate(text: string, max: number): string {
   return text.slice(0, max - 1) + "\u2026";
 }
 
+function isMarkdownFile(file: File) {
+  const name = file.name.toLowerCase();
+  return (
+    name.endsWith(".md") ||
+    name.endsWith(".markdown") ||
+    file.type === "text/markdown"
+  );
+}
+
+function fileBaseName(filename: string) {
+  return filename.replace(/\.[^.]+$/, "");
+}
+
+function slugifyDocumentKey(input: string) {
+  const slug = input
+    .trim()
+    .toLowerCase()
+    .replace(/[^a-z0-9]+/g, "-")
+    .replace(/^-+|-+$/g, "");
+  return slug || "document";
+}
+
+function titleizeFilename(input: string) {
+  return input
+    .split(/[-_ ]+/g)
+    .filter(Boolean)
+    .map((part) => part.charAt(0).toUpperCase() + part.slice(1))
+    .join(" ");
+}
+
 function formatAction(action: string, details?: Record<string, unknown> | null): string {
   if (action === "issue.updated" && details) {
     const previous = (details._previous ?? {}) as Record<string, unknown>;
@@ -132,6 +166,14 @@ function formatAction(action: string, details?: Record<string, unknown> | null):
 
     if (parts.length > 0) return parts.join(", ");
   }
+  if (
+    (action === "issue.document_created" || action === "issue.document_updated" || action === "issue.document_deleted") &&
+    details
+  ) {
+    const key = typeof details.key === "string" ? details.key : "document";
+    const title = typeof details.title === "string" && details.title ? ` (${details.title})` : "";
+    return `${ACTION_LABELS[action] ?? action} ${key}${title}`;
+  }
   return ACTION_LABELS[action] ?? action.replace(/[._]/g, " ");
 }
 
@@ -162,6 +204,7 @@ export function IssueDetail() {
     cost: false,
   });
   const [attachmentError, setAttachmentError] = useState<string | null>(null);
+  const [attachmentDragActive, setAttachmentDragActive] = useState(false);
   const fileInputRef = useRef<HTMLInputElement | null>(null);
   const lastMarkedReadIssueIdRef = useRef<string | null>(null);
 
@@ -402,6 +445,7 @@ export function IssueDetail() {
     queryClient.invalidateQueries({ queryKey: queryKeys.issues.runs(issueId!) });
     queryClient.invalidateQueries({ queryKey: queryKeys.issues.approvals(issueId!) });
     queryClient.invalidateQueries({ queryKey: queryKeys.issues.attachments(issueId!) });
+    queryClient.invalidateQueries({ queryKey: queryKeys.issues.documents(issueId!) });
     queryClient.invalidateQueries({ queryKey: queryKeys.issues.liveRuns(issueId!) });
     queryClient.invalidateQueries({ queryKey: queryKeys.issues.activeRun(issueId!) });
     if (selectedCompanyId) {
@@ -476,6 +520,30 @@ export function IssueDetail() {
     },
   });
 
+  const importMarkdownDocument = useMutation({
+    mutationFn: async (file: File) => {
+      const baseName = fileBaseName(file.name);
+      const key = slugifyDocumentKey(baseName);
+      const existing = (issue?.documentSummaries ?? []).find((doc) => doc.key === key) ?? null;
+      const body = await file.text();
+      const inferredTitle = titleizeFilename(baseName);
+      const nextTitle = existing?.title ?? inferredTitle ?? null;
+      return issuesApi.upsertDocument(issueId!, key, {
+        title: key === "plan" ? null : nextTitle,
+        format: "markdown",
+        body,
+        baseRevisionId: existing?.latestRevisionId ?? null,
+      });
+    },
+    onSuccess: () => {
+      setAttachmentError(null);
+      invalidateIssue();
+    },
+    onError: (err) => {
+      setAttachmentError(err instanceof Error ? err.message : "Document import failed");
+    },
+  });
+
   const deleteAttachment = useMutation({
     mutationFn: (attachmentId: string) => issuesApi.deleteAttachment(attachmentId),
     onSuccess: () => {
@@ -527,15 +595,62 @@ export function IssueDetail() {
   const ancestors = issue.ancestors ?? [];
 
   const handleFilePicked = async (evt: ChangeEvent<HTMLInputElement>) => {
-    const file = evt.target.files?.[0];
-    if (!file) return;
-    await uploadAttachment.mutateAsync(file);
+    const files = evt.target.files;
+    if (!files || files.length === 0) return;
+    for (const file of Array.from(files)) {
+      if (isMarkdownFile(file)) {
+        await importMarkdownDocument.mutateAsync(file);
+      } else {
+        await uploadAttachment.mutateAsync(file);
+      }
+    }
     if (fileInputRef.current) {
       fileInputRef.current.value = "";
     }
   };
 
+  const handleAttachmentDrop = async (evt: DragEvent<HTMLDivElement>) => {
+    evt.preventDefault();
+    setAttachmentDragActive(false);
+    const files = evt.dataTransfer.files;
+    if (!files || files.length === 0) return;
+    for (const file of Array.from(files)) {
+      if (isMarkdownFile(file)) {
+        await importMarkdownDocument.mutateAsync(file);
+      } else {
+        await uploadAttachment.mutateAsync(file);
+      }
+    }
+  };
+
   const isImageAttachment = (attachment: IssueAttachment) => attachment.contentType.startsWith("image/");
+  const attachmentList = attachments ?? [];
+  const hasAttachments = attachmentList.length > 0;
+  const attachmentUploadButton = (
+    <>
+      <input
+        ref={fileInputRef}
+        type="file"
+        accept="image/*,application/pdf,text/plain,text/markdown,application/json,text/csv,text/html,.md,.markdown"
+        className="hidden"
+        onChange={handleFilePicked}
+        multiple
+      />
+      <Button
+        variant="outline"
+        size="sm"
+        onClick={() => fileInputRef.current?.click()}
+        disabled={uploadAttachment.isPending || importMarkdownDocument.isPending}
+        className={cn(
+          "shadow-none",
+          attachmentDragActive && "border-primary bg-primary/5",
+        )}
+      >
+        <Paperclip className="h-3.5 w-3.5 mr-1.5" />
+        {uploadAttachment.isPending || importMarkdownDocument.isPending ? "Uploading..." : "Upload attachment"}
+      </Button>
+    </>
+  );
 
   return (
     <div className="max-w-2xl space-y-6">
@@ -676,14 +791,14 @@ export function IssueDetail() {
 
         <InlineEditor
           value={issue.title}
-          onSave={(title) => updateIssue.mutate({ title })}
+          onSave={(title) => updateIssue.mutateAsync({ title })}
           as="h2"
           className="text-xl font-bold"
         />
 
         <InlineEditor
           value={issue.description ?? ""}
-          onSave={(description) => updateIssue.mutate({ description })}
+          onSave={(description) => updateIssue.mutateAsync({ description })}
           as="p"
           className="text-[15px] leading-7 text-foreground"
           placeholder="Add a description..."
@@ -737,77 +852,86 @@ export function IssueDetail() {
         missingBehavior="placeholder"
       />
 
-      <div className="space-y-3">
+      <IssueDocumentsSection
+        issue={issue}
+        canDeleteDocuments={Boolean(session?.user?.id)}
+        mentions={mentionOptions}
+        imageUploadHandler={async (file) => {
+          const attachment = await uploadAttachment.mutateAsync(file);
+          return attachment.contentPath;
+        }}
+        extraActions={!hasAttachments ? attachmentUploadButton : undefined}
+      />
+
+      {hasAttachments ? (
+        <div
+        className={cn(
+          "space-y-3 rounded-lg transition-colors",
+        )}
+        onDragEnter={(evt) => {
+          evt.preventDefault();
+          setAttachmentDragActive(true);
+        }}
+        onDragOver={(evt) => {
+          evt.preventDefault();
+          setAttachmentDragActive(true);
+        }}
+        onDragLeave={(evt) => {
+          if (evt.currentTarget.contains(evt.relatedTarget as Node | null)) return;
+          setAttachmentDragActive(false);
+        }}
+        onDrop={(evt) => void handleAttachmentDrop(evt)}
+      >
         <div className="flex items-center justify-between gap-2">
           <h3 className="text-sm font-medium text-muted-foreground">Attachments</h3>
-          <div className="flex items-center gap-2">
-            <input
-              ref={fileInputRef}
-              type="file"
-              accept="image/png,image/jpeg,image/webp,image/gif"
-              className="hidden"
-              onChange={handleFilePicked}
-            />
-            <Button
-              variant="outline"
-              size="sm"
-              onClick={() => fileInputRef.current?.click()}
-              disabled={uploadAttachment.isPending}
-            >
-              <Paperclip className="h-3.5 w-3.5 mr-1.5" />
-              {uploadAttachment.isPending ? "Uploading..." : "Upload image"}
-            </Button>
-          </div>
+          {attachmentUploadButton}
         </div>
 
         {attachmentError && (
           <p className="text-xs text-destructive">{attachmentError}</p>
         )}
 
-        {(!attachments || attachments.length === 0) ? (
-          <p className="text-xs text-muted-foreground">No attachments yet.</p>
-        ) : (
-          <div className="space-y-2">
-            {attachments.map((attachment) => (
-              <div key={attachment.id} className="border border-border rounded-md p-2">
-                <div className="flex items-center justify-between gap-2">
-                  <a
-                    href={attachment.contentPath}
-                    target="_blank"
-                    rel="noreferrer"
-                    className="text-xs hover:underline truncate"
-                    title={attachment.originalFilename ?? attachment.id}
-                  >
-                    {attachment.originalFilename ?? attachment.id}
-                  </a>
-                  <button
-                    type="button"
-                    className="text-muted-foreground hover:text-destructive"
-                    onClick={() => deleteAttachment.mutate(attachment.id)}
-                    disabled={deleteAttachment.isPending}
-                    title="Delete attachment"
-                  >
-                    <Trash2 className="h-3.5 w-3.5" />
-                  </button>
-                </div>
-                <p className="text-[11px] text-muted-foreground">
-                  {attachment.contentType} · {(attachment.byteSize / 1024).toFixed(1)} KB
-                </p>
-                {isImageAttachment(attachment) && (
-                  <a href={attachment.contentPath} target="_blank" rel="noreferrer">
-                    <img
-                      src={attachment.contentPath}
-                      alt={attachment.originalFilename ?? "attachment"}
-                      className="mt-2 max-h-56 rounded border border-border object-contain bg-accent/10"
-                      loading="lazy"
-                    />
-                  </a>
-                )}
+        <div className="space-y-2">
+          {attachmentList.map((attachment) => (
+            <div key={attachment.id} className="border border-border rounded-md p-2">
+              <div className="flex items-center justify-between gap-2">
+                <a
+                  href={attachment.contentPath}
+                  target="_blank"
+                  rel="noreferrer"
+                  className="text-xs hover:underline truncate"
+                  title={attachment.originalFilename ?? attachment.id}
+                >
+                  {attachment.originalFilename ?? attachment.id}
+                </a>
+                <button
+                  type="button"
+                  className="text-muted-foreground hover:text-destructive"
+                  onClick={() => deleteAttachment.mutate(attachment.id)}
+                  disabled={deleteAttachment.isPending}
+                  title="Delete attachment"
+                >
+                  <Trash2 className="h-3.5 w-3.5" />
+                </button>
               </div>
-            ))}
-          </div>
-        )}
-      </div>
+              <p className="text-[11px] text-muted-foreground">
+                {attachment.contentType} · {(attachment.byteSize / 1024).toFixed(1)} KB
+              </p>
+              {isImageAttachment(attachment) && (
+                <a href={attachment.contentPath} target="_blank" rel="noreferrer">
+                  <img
+                    src={attachment.contentPath}
+                    alt={attachment.originalFilename ?? "attachment"}
+                    className="mt-2 max-h-56 rounded border border-border object-contain bg-accent/10"
+                    loading="lazy"
+                  />
+                </a>
+              )}
+            </div>
+          ))}
+        </div>
+        </div>
+      ) : null}
 
       <Separator />