Merge pull request #837 from paperclipai/paperclip-issue-documents

feat(issues): add issue documents and inline editing
2026-03-14 09:37:47 -05:00
parent bcce5b7ec2 bc12f08c66
commit 193a987513
33 changed files with 9901 additions and 194 deletions
--- a/doc/SPEC-implementation.md
+++ b/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`
--- a/docs/api/issues.md
+++ b/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
--- a/docs/plans/2026-03-13-issue-documents-plan.md
+++ b/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.
--- a/packages/db/src/migrations/0028_harsh_goliath.sql
+++ b/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");
--- a/packages/db/src/migrations/meta/0028_snapshot.json
+++ b/packages/db/src/migrations/meta/0028_snapshot.json
--- a/packages/db/src/migrations/meta/_journal.json
+++ b/packages/db/src/migrations/meta/_journal.json
@@ -197,6 +197,13 @@
      "when": 1773150731736,
      "tag": "0027_tranquil_tenebrous",
      "breakpoints": true
+    },
+    {
+      "idx": 28,
+      "version": "7",
+      "when": 1773432085646,
+      "tag": "0028_harsh_goliath",
+      "breakpoints": true
    }
  ]
 }
--- a/packages/db/src/schema/document_revisions.ts
+++ b/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,
+    ),
+  }),
+);
--- a/packages/db/src/schema/documents.ts
+++ b/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),
+  }),
+);
--- a/packages/db/src/schema/index.ts
+++ b/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";
--- a/packages/db/src/schema/issue_documents.ts
+++ b/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,
+    ),
+  }),
+);
--- a/packages/shared/src/index.ts
+++ b/packages/shared/src/index.ts
@@ -86,6 +86,11 @@ export type {
  Issue,
  IssueAssigneeAdapterOverrides,
  IssueComment,
+  IssueDocument,
+  IssueDocumentSummary,
+  DocumentRevision,
+  DocumentFormat,
+  LegacyPlanDocument,
  IssueAttachment,
  IssueLabel,
  Goal,
@@ -172,6 +177,9 @@ export {
  addIssueCommentSchema,
  linkIssueApprovalSchema,
  createIssueAttachmentMetadataSchema,
+  issueDocumentFormatSchema,
+  issueDocumentKeySchema,
+  upsertIssueDocumentSchema,
  type CreateIssue,
  type CreateIssueLabel,
  type UpdateIssue,
@@ -179,6 +187,8 @@ export {
  type AddIssueComment,
  type LinkIssueApproval,
  type CreateIssueAttachmentMetadata,
+  type IssueDocumentFormat,
+  type UpsertIssueDocument,
  createGoalSchema,
  updateGoalSchema,
  type CreateGoal,
--- a/packages/shared/src/types/index.ts
+++ b/packages/shared/src/types/index.ts
@@ -23,6 +23,11 @@ export type {
  Issue,
  IssueAssigneeAdapterOverrides,
  IssueComment,
+  IssueDocument,
+  IssueDocumentSummary,
+  DocumentRevision,
+  DocumentFormat,
+  LegacyPlanDocument,
  IssueAncestor,
  IssueAncestorProject,
  IssueAncestorGoal,
--- a/packages/shared/src/types/issue.ts
+++ b/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[];
--- a/packages/shared/src/validators/index.ts
+++ b/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 {
--- a/packages/shared/src/validators/issue.ts
+++ b/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>;
--- a/server/src/tests/documents.test.ts
+++ b/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();
+  });
+});
--- a/server/src/attachment-types.ts
+++ b/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",
 ];

 /**
--- a/server/src/routes/issues.ts
+++ b/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";
@@ -39,6 +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 },
@@ -293,7 +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
@@ -302,6 +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)
@@ -310,6 +315,7 @@ export function issueRoutes(db: Db, storage: StorageService) {
      ...issue,
      goalId: goal?.id ?? issue.goalId,
      ancestors,
+      ...documentPayload,
      project: project ?? null,
      goal: goal ?? null,
      mentionedProjects,
@@ -389,6 +395,146 @@ export function issueRoutes(db: Db, storage: StorageService) {
    });
  });

+  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);
--- a/server/src/services/documents.ts
+++ b/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,
+        };
+      });
+    },
+  };
+}
--- a/server/src/services/index.ts
+++ b/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";
--- a/server/src/services/issues.ts
+++ b/server/src/services/issues.ts
@@ -5,11 +5,13 @@ import {
  assets,
  companies,
  companyMemberships,
+  documents,
  goals,
  heartbeatRuns,
  issueAttachments,
  issueLabels,
  issueComments,
+  issueDocuments,
  issueReadStates,
  issues,
  labels,
@@ -790,6 +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)
@@ -803,6 +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;
--- a/skills/paperclip/SKILL.md
+++ b/skills/paperclip/SKILL.md
@@ -154,6 +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>`
@@ -175,31 +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

@@ -237,6 +237,10 @@ PATCH /api/agents/{agentId}/instructions-path
 | 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`                             |
--- a/ui/src/api/client.ts
+++ b/ui/src/api/client.ts
@@ -41,6 +41,8 @@ export const api = {
    request<T>(path, { method: "POST", body: JSON.stringify(body) }),
  postForm: <T>(path: string, body: FormData) =>
    request<T>(path, { method: "POST", body }),
+  put: <T>(path: string, body: unknown) =>
+    request<T>(path, { method: "PUT", body: JSON.stringify(body) }),
  patch: <T>(path: string, body: unknown) =>
    request<T>(path, { method: "PATCH", body: JSON.stringify(body) }),
  delete: <T>(path: string) => request<T>(path, { method: "DELETE" }),
--- a/ui/src/api/issues.ts
+++ b/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,
--- a/ui/src/components/ActivityRow.tsx
+++ b/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",
--- a/ui/src/components/InlineEditor.tsx
+++ b/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>
  );
 }
--- a/ui/src/components/IssueDocumentsSection.tsx
+++ b/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>
+  );
+}
--- a/ui/src/components/NewIssueDialog.tsx
+++ b/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) */}
--- a/ui/src/context/LiveUpdatesProvider.tsx
+++ b/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) });
      }
--- a/ui/src/hooks/useAutosaveIndicator.ts
+++ b/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,
+  };
+}
--- a/ui/src/index.css
+++ b/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 {
--- a/ui/src/lib/queryKeys.ts
+++ b/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,
--- a/ui/src/pages/IssueDetail.tsx
+++ b/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";
@@ -60,6 +61,9 @@ 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",
@@ -97,6 +101,36 @@ 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>;
@@ -130,6 +164,14 @@ 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, " ");
 }

@@ -160,6 +202,7 @@ 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);

@@ -384,6 +427,7 @@ 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) {
@@ -458,6 +502,30 @@ 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: () => {
@@ -509,15 +577,62 @@ 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">
@@ -658,14 +773,14 @@ 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..."
@@ -678,77 +793,86 @@ export function IssueDetail() {
        />
      </div>

-      <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 />