Server: migration prompts, structured logging, heartbeat reaping, and issue-run tracking

Replace auto-migrate-if-empty with interactive migration flow that inspects pending migrations and prompts before applying. Add pino-pretty for structured console + file logging. Add reapOrphanedRuns to clean up stuck heartbeat runs on startup and periodically. Track runId through auth middleware, activity logs, and all mutation routes. Add issue-run cross-reference queries, live-run and active-run endpoints for issues, issue identifier lookup, reopen-via-comment flow, and done/cancelled -> todo status transitions. Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
2026-02-19 09:09:40 -06:00
parent 21b7bc8da0
commit a90063415e
14 changed files with 605 additions and 67 deletions
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -157,6 +157,9 @@ importers:
      pino-http:
        specifier: ^10.4.0
        version: 10.5.0
+      pino-pretty:
+        specifier: ^13.1.3
+        version: 13.1.3
      ws:
        specifier: ^8.19.0
        version: 8.19.0
@@ -2027,6 +2030,9 @@ packages:
      react: ^18 || ^19 || ^19.0.0-rc
      react-dom: ^18 || ^19 || ^19.0.0-rc

+  colorette@2.0.20:
+    resolution: {integrity: sha512-IfEDxwoWIjkeXL1eXcDiow4UbKjhLdq6/EuSVR9GMN7KVH3r9gQ83e73hsz1Nd1T3ijd5xv1wcWRYO+D6kCI2w==}
+
  combined-stream@1.0.8:
    resolution: {integrity: sha512-FQN4MRfuJeHf7cBbBMJFXhKSDq+2kAArBlmRBvcvFE5BB1HZKXtSFASDhdlz9zOYwxh8lDdnvmMOe/+5cdoEdg==}
    engines: {node: '>= 0.8'}
@@ -2067,6 +2073,9 @@ packages:
  csstype@3.2.3:
    resolution: {integrity: sha512-z1HGKcYy2xA8AGQfwrn0PAy+PB7X/GSj3UVJW9qKyn43xWa+gl5nXmU4qqLMRzWVLFC8KusUX8T/0kCiOYpAIQ==}

+  dateformat@4.6.3:
+    resolution: {integrity: sha512-2P0p0pFGzHS5EMnhdxQi7aJN+iMheud0UhG4dlE1DLAlvL8JHjJJTX/CSm4JXwV0Ka5nGk3zC5mcb5bUQUxxMA==}
+
  debug@4.4.3:
    resolution: {integrity: sha512-RGwwWnwQvkVfavKVt22FGLw+xYSdzARwm0ru6DhTVA3umU5hZc28V3kO4stgYryrTlLpuvgI9GiijltAjNbcqA==}
    engines: {node: '>=6.0'}
@@ -2221,6 +2230,9 @@ packages:
    resolution: {integrity: sha512-Q0n9HRi4m6JuGIV1eFlmvJB7ZEVxu93IrMyiMsGC0lrMJMWzRgx6WGquyfQgZVb31vhGgXnfmPNNXmxnOkRBrg==}
    engines: {node: '>= 0.8'}

+  end-of-stream@1.4.5:
+    resolution: {integrity: sha512-ooEGc6HP26xXq/N+GCGOT0JKCLDGrq2bQUZrQ7gyrJiZANJ/8YDTxTpQBXGMn+WbIQXNVpyWymm7KYVICQnyOg==}
+
  enhanced-resolve@5.19.0:
    resolution: {integrity: sha512-phv3E1Xl4tQOShqSte26C7Fl84EwUdZsyOuSSk9qtAGyyQs2s3jJzComh+Abf4g187lUUAvH+H26omrqia2aGg==}
    engines: {node: '>=10.13.0'}
@@ -2286,6 +2298,9 @@ packages:
    resolution: {integrity: sha512-hIS4idWWai69NezIdRt2xFVofaF4j+6INOpJlVOLDO8zXGpUVEVzIYk12UUi2JzjEzWL3IOAxcTubgz9Po0yXw==}
    engines: {node: '>= 18'}

+  fast-copy@4.0.2:
+    resolution: {integrity: sha512-ybA6PDXIXOXivLJK/z9e+Otk7ve13I4ckBvGO5I2RRmBU1gMHLVDJYEuJYhGwez7YNlYji2M2DvVU+a9mSFDlw==}
+
  fast-safe-stringify@2.1.1:
    resolution: {integrity: sha512-W+KJc2dmILlPplD/H4K9l9LcAHAfPtP6BY84uVLXQ6Evcz9Lcg33Y2z1IVblT6xdY54PXYVHEv+0Wpq8Io6zkA==}

@@ -2368,6 +2383,9 @@ packages:
    resolution: {integrity: sha512-0hJU9SCPvmMzIBdZFqNPXWa6dqh7WdH0cII9y+CyS8rG3nL48Bclra9HmKhVVUHyPWNH5Y7xDwAB7bfgSjkUMQ==}
    engines: {node: '>= 0.4'}

+  help-me@5.0.0:
+    resolution: {integrity: sha512-7xgomUX6ADmcYzFik0HzAxh/73YlKR9bmFzf51CZwR+b6YtzU2m0u49hQCqV6SvlqIqsaxovfwdvbnsw3b/zpg==}
+
  http-errors@2.0.1:
    resolution: {integrity: sha512-4FbRdAX+bSdmo4AUFuS0WNiPz8NgFt+r8ThgNWmlrjQjt1Q7ZR9+zTlce2859x4KSXrwIsaeTqDoKQmtP8pLmQ==}
    engines: {node: '>= 0.8'}
@@ -2390,6 +2408,10 @@ packages:
    resolution: {integrity: sha512-ekilCSN1jwRvIbgeg/57YFh8qQDNbwDb9xT/qu2DAHbFFZUicIl4ygVaAvzveMhMVr3LnpSKTNnwt8PoOfmKhQ==}
    hasBin: true

+  joycon@3.1.1:
+    resolution: {integrity: sha512-34wB/Y7MW7bzjKRjUKTa46I2Z7eV62Rkhva+KkopW7Qvv/OSWBqvkSY7vusOPrNuZcUG3tApvdVgNB8POj3SPw==}
+    engines: {node: '>=10'}
+
  js-tokens@4.0.0:
    resolution: {integrity: sha512-RdJUflcE3cUzKiMqQgsCu06FPu9UdIJO0beYbPhHN4k6apgJtifcoCtT9bcxOpYBtpD2kCM6Sbzg4CausW/PKQ==}

@@ -2527,6 +2549,9 @@ packages:
    engines: {node: '>=4.0.0'}
    hasBin: true

+  minimist@1.2.8:
+    resolution: {integrity: sha512-2yyAR8qBkN3YuheJanUpWC5U3bb5osDywNB8RzDVlDwDHbocAJveqqj1u8+SVD7jkWT4yvsHCpWqqWqAxb0zCA==}
+
  ms@2.1.3:
    resolution: {integrity: sha512-6FlzubTLZG3J2a/NVCAleEhjzq5oxgHyaCU9yYXvcLsvoVaHJq/s5xXI6/XXP6tz7R9xAOtHnSO/tXtF3WRTlA==}

@@ -2615,9 +2640,16 @@ packages:
  pino-abstract-transport@2.0.0:
    resolution: {integrity: sha512-F63x5tizV6WCh4R6RHyi2Ml+M70DNRXt/+HANowMflpgGFMAym/VKm6G7ZOQRjqN7XbGxK1Lg9t6ZrtzOaivMw==}

+  pino-abstract-transport@3.0.0:
+    resolution: {integrity: sha512-wlfUczU+n7Hy/Ha5j9a/gZNy7We5+cXp8YL+X+PG8S0KXxw7n/JXA3c46Y0zQznIJ83URJiwy7Lh56WLokNuxg==}
+
  pino-http@10.5.0:
    resolution: {integrity: sha512-hD91XjgaKkSsdn8P7LaebrNzhGTdB086W3pyPihX0EzGPjq5uBJBXo4N5guqNaK6mUjg9aubMF7wDViYek9dRA==}

+  pino-pretty@13.1.3:
+    resolution: {integrity: sha512-ttXRkkOz6WWC95KeY9+xxWL6AtImwbyMHrL1mSwqwW9u+vLp/WIElvHvCSDg0xO/Dzrggz1zv3rN5ovTRVowKg==}
+    hasBin: true
+
  pino-std-serializers@7.1.0:
    resolution: {integrity: sha512-BndPH67/JxGExRgiX1dX0w1FvZck5Wa4aal9198SrRhZjH3GxKQUKIBnYJTdj2HDN3UQAS06HlfcSbQj2OHmaw==}

@@ -2656,6 +2688,9 @@ packages:
    resolution: {integrity: sha512-llQsMLSUDUPT44jdrU/O37qlnifitDP+ZwrmmZcoSKyLKvtZxpyV0n2/bD/N4tBAAZ/gJEdZU7KMraoK1+XYAg==}
    engines: {node: '>= 0.10'}

+  pump@3.0.3:
+    resolution: {integrity: sha512-todwxLMY7/heScKmntwQG8CXVkWUOdYxIvY2s0VWAAMh/nd8SoYiRaKjlr7+iCs984f2P8zvrfWcDDYVb73NfA==}
+
  qs@6.15.0:
    resolution: {integrity: sha512-mAZTtNCeetKMH+pSjrb76NAM8V9a05I9aBZOHztWy/UqcJdQYNsf59vrRKWnojAT9Y+GbIvoTBC++CPHqpDBhQ==}
    engines: {node: '>=0.6'}
@@ -2770,6 +2805,9 @@ packages:
  scheduler@0.27.0:
    resolution: {integrity: sha512-eNv+WrVbKu1f3vbYJT/xtiF5syA5HPIMtf9IgY/nKg0sWqzAUEvqY/xm7OcZc/qafLx/iO9FgOmeSAp4v5ti/Q==}

+  secure-json-parse@4.1.0:
+    resolution: {integrity: sha512-l4KnYfEyqYJxDwlNVyRfO2E4NTHfMKAWdUuA8J0yve2Dz/E/PdBepY03RvyJpssIpRFwJoCD55wA+mEDs6ByWA==}
+
  semver@6.3.1:
    resolution: {integrity: sha512-BR7VvDCVHO+q2xBEWskxS6DJE1qRnb7DxzUrogb71CWoSficBxYsiAGd+Kl0mmq/MprG9yArRkyrQxTO6XjMzA==}
    hasBin: true
@@ -2838,6 +2876,10 @@ packages:
  std-env@3.10.0:
    resolution: {integrity: sha512-5GS12FdOZNliM5mAOxFRg7Ir0pWz8MdpYm6AY6VPkGpbA7ZzmbzNcBJQ0GPvvyWgcY7QAhCgf9Uy89I03faLkg==}

+  strip-json-comments@5.0.3:
+    resolution: {integrity: sha512-1tB5mhVo7U+ETBKNf92xT4hrQa3pm0MZ0PQvuDnWgAAGHDsfp4lPSpiS6psrSiet87wyGPh9ft6wmhOMQ0hDiw==}
+    engines: {node: '>=14.16'}
+
  strip-literal@3.1.0:
    resolution: {integrity: sha512-8r3mkIM/2+PpjHoOtiAW8Rg3jJLHaV7xPwG+YRGrv6FP0wwk/toTpATxWYOW0BKdWwl82VT2tFYi5DlROa0Mxg==}

@@ -4674,6 +4716,8 @@ snapshots:
      - '@types/react'
      - '@types/react-dom'

+  colorette@2.0.20: {}
+
  combined-stream@1.0.8:
    dependencies:
      delayed-stream: 1.0.0
@@ -4698,6 +4742,8 @@ snapshots:

  csstype@3.2.3: {}

+  dateformat@4.6.3: {}
+
  debug@4.4.3:
    dependencies:
      ms: 2.1.3
@@ -4769,6 +4815,10 @@ snapshots:

  encodeurl@2.0.0: {}

+  end-of-stream@1.4.5:
+    dependencies:
+      once: 1.4.0
+
  enhanced-resolve@5.19.0:
    dependencies:
      graceful-fs: 4.2.11
@@ -4926,6 +4976,8 @@ snapshots:
    transitivePeerDependencies:
      - supports-color

+  fast-copy@4.0.2: {}
+
  fast-safe-stringify@2.1.1: {}

  fdir@6.5.0(picomatch@4.0.3):
@@ -5008,6 +5060,8 @@ snapshots:
    dependencies:
      function-bind: 1.1.2

+  help-me@5.0.0: {}
+
  http-errors@2.0.1:
    dependencies:
      depd: 2.0.0
@@ -5028,6 +5082,8 @@ snapshots:

  jiti@2.6.1: {}

+  joycon@3.1.1: {}
+
  js-tokens@4.0.0: {}

  js-tokens@9.0.1: {}
@@ -5121,6 +5177,8 @@ snapshots:

  mime@2.6.0: {}

+  minimist@1.2.8: {}
+
  ms@2.1.3: {}

  nanoid@3.3.11: {}
@@ -5199,6 +5257,10 @@ snapshots:
    dependencies:
      split2: 4.2.0

+  pino-abstract-transport@3.0.0:
+    dependencies:
+      split2: 4.2.0
+
  pino-http@10.5.0:
    dependencies:
      get-caller-file: 2.0.5
@@ -5206,6 +5268,22 @@ snapshots:
      pino-std-serializers: 7.1.0
      process-warning: 5.0.0

+  pino-pretty@13.1.3:
+    dependencies:
+      colorette: 2.0.20
+      dateformat: 4.6.3
+      fast-copy: 4.0.2
+      fast-safe-stringify: 2.1.1
+      help-me: 5.0.0
+      joycon: 3.1.1
+      minimist: 1.2.8
+      on-exit-leak-free: 2.1.2
+      pino-abstract-transport: 3.0.0
+      pump: 3.0.3
+      secure-json-parse: 4.1.0
+      sonic-boom: 4.2.1
+      strip-json-comments: 5.0.3
+
  pino-std-serializers@7.1.0: {}

  pino@9.14.0:
@@ -5251,6 +5329,11 @@ snapshots:
      forwarded: 0.2.0
      ipaddr.js: 1.9.1

+  pump@3.0.3:
+    dependencies:
+      end-of-stream: 1.4.5
+      once: 1.4.0
+
  qs@6.15.0:
    dependencies:
      side-channel: 1.1.0
@@ -5430,6 +5513,8 @@ snapshots:

  scheduler@0.27.0: {}

+  secure-json-parse@4.1.0: {}
+
  semver@6.3.1: {}

  send@1.2.1:
@@ -5514,6 +5599,8 @@ snapshots:

  std-env@3.10.0: {}

+  strip-json-comments@5.0.3: {}
+
  strip-literal@3.1.0:
    dependencies:
      js-tokens: 9.0.1
--- a/server/package.json
+++ b/server/package.json
@@ -15,12 +15,13 @@
    "@paperclip/adapter-utils": "workspace:*",
    "@paperclip/db": "workspace:*",
    "@paperclip/shared": "workspace:*",
-    "dotenv": "^17.0.1",
    "detect-port": "^2.1.0",
+    "dotenv": "^17.0.1",
    "drizzle-orm": "^0.38.4",
    "express": "^5.1.0",
    "pino": "^9.6.0",
    "pino-http": "^10.4.0",
+    "pino-pretty": "^13.1.3",
    "ws": "^8.19.0",
    "zod": "^3.24.2"
  },
--- a/server/src/index.ts
+++ b/server/src/index.ts
@@ -1,10 +1,13 @@
 import { existsSync, readFileSync, rmSync } from "node:fs";
 import { createServer } from "node:http";
 import { resolve } from "node:path";
+import { createInterface } from "node:readline/promises";
+import { stdin, stdout } from "node:process";
 import {
  createDb,
  ensurePostgresDatabase,
-  migratePostgresIfEmpty,
+  inspectMigrations,
+  applyPendingMigrations,
 } from "@paperclip/db";
 import detectPort from "detect-port";
 import { createApp } from "./app.js";
@@ -30,27 +33,80 @@ type EmbeddedPostgresCtor = new (opts: {

 const config = loadConfig();

+type MigrationSummary =
+  | "skipped"
+  | "already applied"
+  | "applied (empty database)"
+  | "applied (pending migrations)"
+  | "pending migrations skipped";
+
+function formatPendingMigrationSummary(migrations: string[]): string {
+  if (migrations.length === 0) return "none";
+  return migrations.length > 3
+    ? `${migrations.slice(0, 3).join(", ")} (+${migrations.length - 3} more)`
+    : migrations.join(", ");
+}
+
+async function promptApplyMigrations(migrations: string[]): Promise<boolean> {
+  if (!stdin.isTTY || !stdout.isTTY) return true;
+  if (process.env.PAPERCLIP_MIGRATION_AUTO_APPLY === "true") return true;
+
+  const prompt = createInterface({ input: stdin, output: stdout });
+  try {
+    const answer = (await prompt.question(
+      `Apply pending migrations (${formatPendingMigrationSummary(migrations)}) now? (y/N): `,
+    )).trim().toLowerCase();
+    return answer === "y" || answer === "yes";
+  } finally {
+    prompt.close();
+  }
+}
+
+async function ensureMigrations(connectionString: string, label: string): Promise<MigrationSummary> {
+  const state = await inspectMigrations(connectionString);
+  if (state.status === "upToDate") return "already applied";
+  if (state.status === "needsMigrations" && state.reason === "no-migration-journal-non-empty-db") {
+    logger.warn(
+      { tableCount: state.tableCount },
+      `${label} has existing tables but no migration journal. Run migrations manually to sync schema.`,
+    );
+    const apply = await promptApplyMigrations(state.pendingMigrations);
+    if (!apply) {
+      logger.warn(
+        { pendingMigrations: state.pendingMigrations },
+        `${label} has pending migrations; continuing without applying. Run pnpm db:migrate to apply before startup.`,
+      );
+      return "pending migrations skipped";
+    }
+
+    logger.info({ pendingMigrations: state.pendingMigrations }, `Applying ${state.pendingMigrations.length} pending migrations for ${label}`);
+    await applyPendingMigrations(connectionString);
+    return "applied (pending migrations)";
+  }
+
+  const apply = await promptApplyMigrations(state.pendingMigrations);
+  if (!apply) {
+    logger.warn(
+      { pendingMigrations: state.pendingMigrations },
+      `${label} has pending migrations; continuing without applying. Run pnpm db:migrate to apply before startup.`,
+    );
+    return "pending migrations skipped";
+  }
+
+  logger.info({ pendingMigrations: state.pendingMigrations }, `Applying ${state.pendingMigrations.length} pending migrations for ${label}`);
+  await applyPendingMigrations(connectionString);
+  return "applied (pending migrations)";
+}
+
 let db;
 let embeddedPostgres: EmbeddedPostgresInstance | null = null;
 let embeddedPostgresStartedByThisProcess = false;
-let migrationSummary = "skipped";
+let migrationSummary: MigrationSummary = "skipped";
 let startupDbInfo:
  | { mode: "external-postgres"; connectionString: string }
  | { mode: "embedded-postgres"; dataDir: string; port: number };
 if (config.databaseUrl) {
-  const migration = await migratePostgresIfEmpty(config.databaseUrl);
-  if (migration.migrated) {
-    logger.info("Empty PostgreSQL database detected; applied migrations");
-    migrationSummary = "applied (empty database)";
-  } else if (migration.reason === "not-empty-no-migration-journal") {
-    logger.warn(
-      { tableCount: migration.tableCount },
-      "PostgreSQL has existing tables but no migration journal; skipped auto-migrate",
-    );
-    migrationSummary = "skipped (existing schema, no migration journal)";
-  } else {
-    migrationSummary = "already applied";
-  }
+  migrationSummary = await ensureMigrations(config.databaseUrl, "PostgreSQL");

  db = createDb(config.databaseUrl);
  logger.info("Using external PostgreSQL via DATABASE_URL/config");
@@ -131,19 +187,7 @@ if (config.databaseUrl) {
  }

  const embeddedConnectionString = `postgres://paperclip:paperclip@127.0.0.1:${port}/paperclip`;
-  const migration = await migratePostgresIfEmpty(embeddedConnectionString);
-  if (migration.migrated) {
-    logger.info("Empty embedded PostgreSQL database detected; applied migrations");
-    migrationSummary = "applied (empty database)";
-  } else if (migration.reason === "not-empty-no-migration-journal") {
-    logger.warn(
-      { tableCount: migration.tableCount },
-      "Embedded PostgreSQL has existing tables but no migration journal; skipped auto-migrate",
-    );
-    migrationSummary = "skipped (existing schema, no migration journal)";
-  } else {
-    migrationSummary = "already applied";
-  }
+  migrationSummary = await ensureMigrations(embeddedConnectionString, "Embedded PostgreSQL");

  db = createDb(embeddedConnectionString);
  logger.info("Embedded PostgreSQL ready");
@@ -163,6 +207,12 @@ setupLiveEventsWebSocketServer(server, db as any);

 if (config.heartbeatSchedulerEnabled) {
  const heartbeat = heartbeatService(db as any);
+
+  // Reap orphaned runs at startup (no threshold -- runningProcesses is empty)
+  void heartbeat.reapOrphanedRuns().catch((err) => {
+    logger.error({ err }, "startup reap of orphaned heartbeat runs failed");
+  });
+
  setInterval(() => {
    void heartbeat
      .tickTimers(new Date())
@@ -174,6 +224,13 @@ if (config.heartbeatSchedulerEnabled) {
      .catch((err) => {
        logger.error({ err }, "heartbeat timer tick failed");
      });
+
+    // Periodically reap orphaned runs (5-min staleness threshold)
+    void heartbeat
+      .reapOrphanedRuns({ staleThresholdMs: 5 * 60 * 1000 })
+      .catch((err) => {
+        logger.error({ err }, "periodic reap of orphaned heartbeat runs failed");
+      });
  }, config.heartbeatSchedulerIntervalMs);
 }

--- a/server/src/middleware/auth.ts
+++ b/server/src/middleware/auth.ts
@@ -13,8 +13,11 @@ export function actorMiddleware(db: Db): RequestHandler {
  return async (req, _res, next) => {
    req.actor = { type: "board", userId: "board" };

+    const runIdHeader = req.header("x-paperclip-run-id");
+
    const authHeader = req.header("authorization");
    if (!authHeader?.toLowerCase().startsWith("bearer ")) {
+      if (runIdHeader) req.actor.runId = runIdHeader;
      next();
      return;
    }
@@ -60,6 +63,7 @@ export function actorMiddleware(db: Db): RequestHandler {
        agentId: claims.sub,
        companyId: claims.company_id,
        keyId: undefined,
+        runId: runIdHeader || undefined,
      };
      next();
      return;
@@ -75,6 +79,7 @@ export function actorMiddleware(db: Db): RequestHandler {
      agentId: key.agentId,
      companyId: key.companyId,
      keyId: key.id,
+      runId: runIdHeader || undefined,
    };

    next();
--- a/server/src/middleware/logger.ts
+++ b/server/src/middleware/logger.ts
@@ -1,5 +1,41 @@
+import path from "node:path";
+import fs from "node:fs";
 import pino from "pino";
 import { pinoHttp } from "pino-http";

-export const logger = pino();
-export const httpLogger = pinoHttp({ logger });
+const logDir = path.resolve(process.cwd(), ".paperclip", "logs");
+fs.mkdirSync(logDir, { recursive: true });
+
+const logFile = path.join(logDir, "server.log");
+
+const sharedOpts = {
+  translateTime: "HH:MM:ss",
+  ignore: "pid,hostname",
+};
+
+export const logger = pino({
+  level: "debug",
+}, pino.transport({
+  targets: [
+    {
+      target: "pino-pretty",
+      options: { ...sharedOpts, ignore: "pid,hostname,req,res", hideObject: true, colorize: true, destination: 1 },
+      level: "info",
+    },
+    {
+      target: "pino-pretty",
+      options: { ...sharedOpts, colorize: false, destination: logFile, mkdir: true },
+      level: "debug",
+    },
+  ],
+}));
+
+export const httpLogger = pinoHttp({
+  logger,
+  customSuccessMessage(req, res) {
+    return `${req.method} ${req.url} ${res.statusCode}`;
+  },
+  customErrorMessage(req, res) {
+    return `${req.method} ${req.url} ${res.statusCode}`;
+  },
+});
--- a/server/src/routes/activity.ts
+++ b/server/src/routes/activity.ts
@@ -4,6 +4,7 @@ import type { Db } from "@paperclip/db";
 import { validate } from "../middleware/validate.js";
 import { activityService } from "../services/activity.js";
 import { assertBoard, assertCompanyAccess } from "./authz.js";
+import { issueService } from "../services/index.js";

 const createActivitySchema = z.object({
  actorType: z.enum(["agent", "user", "system"]).optional().default("system"),
@@ -18,6 +19,7 @@ const createActivitySchema = z.object({
 export function activityRoutes(db: Db) {
  const router = Router();
  const svc = activityService(db);
+  const issueSvc = issueService(db);

  router.get("/companies/:companyId/activity", async (req, res) => {
    const companyId = req.params.companyId as string;
@@ -43,5 +45,35 @@ export function activityRoutes(db: Db) {
    res.status(201).json(event);
  });

+  router.get("/issues/:id/activity", async (req, res) => {
+    const id = req.params.id as string;
+    const issue = await issueSvc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+    const result = await svc.forIssue(id);
+    res.json(result);
+  });
+
+  router.get("/issues/:id/runs", async (req, res) => {
+    const id = req.params.id as string;
+    const issue = await issueSvc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+    const result = await svc.runsForIssue(id);
+    res.json(result);
+  });
+
+  router.get("/heartbeat-runs/:runId/issues", async (req, res) => {
+    const runId = req.params.runId as string;
+    const result = await svc.issuesForRun(runId);
+    res.json(result);
+  });
+
  return router;
 }
--- a/server/src/routes/agents.ts
+++ b/server/src/routes/agents.ts
@@ -1,5 +1,7 @@
 import { Router } from "express";
 import type { Db } from "@paperclip/db";
+import { agents as agentsTable, heartbeatRuns } from "@paperclip/db";
+import { and, desc, eq, inArray, sql } from "drizzle-orm";
 import {
  createAgentKeySchema,
  createAgentSchema,
@@ -7,7 +9,7 @@ import {
  updateAgentSchema,
 } from "@paperclip/shared";
 import { validate } from "../middleware/validate.js";
-import { agentService, heartbeatService, logActivity } from "../services/index.js";
+import { agentService, heartbeatService, issueService, logActivity } from "../services/index.js";
 import { assertBoard, assertCompanyAccess, getActorInfo } from "./authz.js";
 import { listAdapterModels } from "../adapters/index.js";

@@ -160,6 +162,7 @@ export function agentRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "agent.created",
      entityType: "agent",
      entityId: agent.id,
@@ -195,6 +198,7 @@ export function agentRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "agent.updated",
      entityType: "agent",
      entityId: agent.id,
@@ -349,6 +353,7 @@ export function agentRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "heartbeat.invoked",
      entityType: "heartbeat_run",
      entityId: run.id,
@@ -397,6 +402,7 @@ export function agentRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "heartbeat.invoked",
      entityType: "heartbeat_run",
      entityId: run.id,
@@ -472,5 +478,77 @@ export function agentRoutes(db: Db) {
    res.json(result);
  });

+  router.get("/issues/:id/live-runs", async (req, res) => {
+    const id = req.params.id as string;
+    const issueSvc = issueService(db);
+    const issue = await issueSvc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+
+    const liveRuns = await db
+      .select({
+        id: heartbeatRuns.id,
+        status: heartbeatRuns.status,
+        invocationSource: heartbeatRuns.invocationSource,
+        triggerDetail: heartbeatRuns.triggerDetail,
+        startedAt: heartbeatRuns.startedAt,
+        finishedAt: heartbeatRuns.finishedAt,
+        createdAt: heartbeatRuns.createdAt,
+        agentId: heartbeatRuns.agentId,
+        agentName: agentsTable.name,
+        adapterType: agentsTable.adapterType,
+      })
+      .from(heartbeatRuns)
+      .innerJoin(agentsTable, eq(heartbeatRuns.agentId, agentsTable.id))
+      .where(
+        and(
+          eq(heartbeatRuns.companyId, issue.companyId),
+          inArray(heartbeatRuns.status, ["queued", "running"]),
+          sql`${heartbeatRuns.contextSnapshot} ->> 'issueId' = ${id}`,
+        ),
+      )
+      .orderBy(desc(heartbeatRuns.createdAt));
+
+    res.json(liveRuns);
+  });
+
+  router.get("/issues/:id/active-run", async (req, res) => {
+    const id = req.params.id as string;
+    const issueSvc = issueService(db);
+    const issue = await issueSvc.getById(id);
+    if (!issue) {
+      res.status(404).json({ error: "Issue not found" });
+      return;
+    }
+    assertCompanyAccess(req, issue.companyId);
+
+    if (!issue.assigneeAgentId || issue.status !== "in_progress") {
+      res.json(null);
+      return;
+    }
+
+    const agent = await svc.getById(issue.assigneeAgentId);
+    if (!agent) {
+      res.json(null);
+      return;
+    }
+
+    const run = await heartbeat.getActiveRunForAgent(issue.assigneeAgentId);
+    if (!run) {
+      res.json(null);
+      return;
+    }
+
+    res.json({
+      ...run,
+      agentId: agent.id,
+      agentName: agent.name,
+      adapterType: agent.adapterType,
+    });
+  });
+
  return router;
 }
--- a/server/src/routes/authz.ts
+++ b/server/src/routes/authz.ts
@@ -19,6 +19,7 @@ export function getActorInfo(req: Request) {
      actorType: "agent" as const,
      actorId: req.actor.agentId ?? "unknown-agent",
      agentId: req.actor.agentId ?? null,
+      runId: req.actor.runId ?? null,
    };
  }

@@ -26,5 +27,6 @@ export function getActorInfo(req: Request) {
    actorType: "user" as const,
    actorId: req.actor.userId ?? "board",
    agentId: null,
+    runId: req.actor.runId ?? null,
  };
 }
--- a/server/src/routes/issues.ts
+++ b/server/src/routes/issues.ts
@@ -29,13 +29,14 @@ export function issueRoutes(db: Db) {

  router.get("/issues/:id", async (req, res) => {
    const id = req.params.id as string;
-    const issue = await svc.getById(id);
+    const isIdentifier = /^[A-Z]+-\d+$/i.test(id);
+    const issue = isIdentifier ? await svc.getByIdentifier(id) : await svc.getById(id);
    if (!issue) {
      res.status(404).json({ error: "Issue not found" });
      return;
    }
    assertCompanyAccess(req, issue.companyId);
-    const ancestors = await svc.getAncestors(id);
+    const ancestors = await svc.getAncestors(issue.id);
    res.json({ ...issue, ancestors });
  });

@@ -55,6 +56,7 @@ export function issueRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "issue.created",
      entityType: "issue",
      entityId: issue.id,
@@ -100,6 +102,7 @@ export function issueRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "issue.updated",
      entityType: "issue",
      entityId: issue.id,
@@ -118,6 +121,7 @@ export function issueRoutes(db: Db) {
        actorType: actor.actorType,
        actorId: actor.actorId,
        agentId: actor.agentId,
+        runId: actor.runId,
        action: "issue.comment_added",
        entityType: "issue",
        entityId: issue.id,
@@ -142,16 +146,20 @@ export function issueRoutes(db: Db) {

    const assigneeChanged =
      req.body.assigneeAgentId !== undefined && req.body.assigneeAgentId !== existing.assigneeAgentId;
-    if (assigneeChanged && issue.assigneeAgentId) {
+    const reopened =
+      (existing.status === "done" || existing.status === "cancelled") &&
+      issue.status !== "done" && issue.status !== "cancelled";
+
+    if ((assigneeChanged || reopened) && issue.assigneeAgentId) {
      void heartbeat
        .wakeup(issue.assigneeAgentId, {
-          source: "assignment",
+          source: reopened ? "automation" : "assignment",
          triggerDetail: "system",
-          reason: "issue_assigned",
+          reason: reopened ? "issue_reopened" : "issue_assigned",
          payload: { issueId: issue.id, mutation: "update" },
          requestedByActorType: actor.actorType,
          requestedByActorId: actor.actorId,
-          contextSnapshot: { issueId: issue.id, source: "issue.update" },
+          contextSnapshot: { issueId: issue.id, source: reopened ? "issue.reopen" : "issue.update" },
        })
        .catch((err) => logger.warn({ err, issueId: issue.id }, "failed to wake assignee on issue update"));
    }
@@ -180,6 +188,7 @@ export function issueRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "issue.deleted",
      entityType: "issue",
      entityId: issue.id,
@@ -210,6 +219,7 @@ export function issueRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "issue.checked_out",
      entityType: "issue",
      entityId: issue.id,
@@ -252,6 +262,7 @@ export function issueRoutes(db: Db) {
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "issue.released",
      entityType: "issue",
      entityId: released.id,
@@ -282,19 +293,54 @@ export function issueRoutes(db: Db) {
    assertCompanyAccess(req, issue.companyId);

    const actor = getActorInfo(req);
+    const reopenRequested = req.body.reopen === true;
+    const isClosed = issue.status === "done" || issue.status === "cancelled";
+    let reopened = false;
+    let reopenFromStatus: string | null = null;
+    let currentIssue = issue;
+
+    if (reopenRequested && isClosed) {
+      const reopenedIssue = await svc.update(id, { status: "todo" });
+      if (!reopenedIssue) {
+        res.status(404).json({ error: "Issue not found" });
+        return;
+      }
+      reopened = true;
+      reopenFromStatus = issue.status;
+      currentIssue = reopenedIssue;
+
+      await logActivity(db, {
+        companyId: currentIssue.companyId,
+        actorType: actor.actorType,
+        actorId: actor.actorId,
+        agentId: actor.agentId,
+        runId: actor.runId,
+        action: "issue.updated",
+        entityType: "issue",
+        entityId: currentIssue.id,
+        details: {
+          status: "todo",
+          reopened: true,
+          reopenedFrom: reopenFromStatus,
+          source: "comment",
+        },
+      });
+    }
+
    const comment = await svc.addComment(id, req.body.body, {
      agentId: actor.agentId ?? undefined,
      userId: actor.actorType === "user" ? actor.actorId : undefined,
    });

    await logActivity(db, {
-      companyId: issue.companyId,
+      companyId: currentIssue.companyId,
      actorType: actor.actorType,
      actorId: actor.actorId,
      agentId: actor.agentId,
+      runId: actor.runId,
      action: "issue.comment_added",
      entityType: "issue",
-      entityId: issue.id,
+      entityId: currentIssue.id,
      details: { commentId: comment.id },
    });

@@ -313,6 +359,32 @@ export function issueRoutes(db: Db) {
      }
    }).catch((err) => logger.warn({ err, issueId: id }, "failed to resolve @-mentions"));

+    if (reopened && currentIssue.assigneeAgentId) {
+      void heartbeat
+        .wakeup(currentIssue.assigneeAgentId, {
+          source: "automation",
+          triggerDetail: "system",
+          reason: "issue_reopened_via_comment",
+          payload: {
+            issueId: currentIssue.id,
+            commentId: comment.id,
+            reopenedFrom: reopenFromStatus,
+            mutation: "comment",
+          },
+          requestedByActorType: actor.actorType,
+          requestedByActorId: actor.actorId,
+          contextSnapshot: {
+            issueId: currentIssue.id,
+            taskId: currentIssue.id,
+            commentId: comment.id,
+            source: "issue.comment.reopen",
+            wakeReason: "issue_reopened_via_comment",
+            reopenedFrom: reopenFromStatus,
+          },
+        })
+        .catch((err) => logger.warn({ err, issueId: currentIssue.id }, "failed to wake assignee on issue reopen comment"));
+    }
+
    res.status(201).json(comment);
  });

--- a/server/src/services/activity-log.ts
+++ b/server/src/services/activity-log.ts
@@ -10,6 +10,7 @@ export interface LogActivityInput {
  entityType: string;
  entityId: string;
  agentId?: string | null;
+  runId?: string | null;
  details?: Record<string, unknown> | null;
 }

@@ -22,6 +23,7 @@ export async function logActivity(db: Db, input: LogActivityInput) {
    entityType: input.entityType,
    entityId: input.entityId,
    agentId: input.agentId ?? null,
+    runId: input.runId ?? null,
    details: input.details ?? null,
  });

@@ -35,6 +37,7 @@ export async function logActivity(db: Db, input: LogActivityInput) {
      entityType: input.entityType,
      entityId: input.entityId,
      agentId: input.agentId ?? null,
+      runId: input.runId ?? null,
      details: input.details ?? null,
    },
  });
--- a/server/src/services/activity.ts
+++ b/server/src/services/activity.ts
@@ -1,6 +1,6 @@
-import { and, desc, eq } from "drizzle-orm";
+import { and, desc, eq, isNotNull, sql } from "drizzle-orm";
 import type { Db } from "@paperclip/db";
-import { activityLog } from "@paperclip/db";
+import { activityLog, heartbeatRuns, issues } from "@paperclip/db";

 export interface ActivityFilters {
  companyId: string;
@@ -10,6 +10,7 @@ export interface ActivityFilters {
 }

 export function activityService(db: Db) {
+  const issueIdAsText = sql<string>`${issues.id}::text`;
  return {
    list: (filters: ActivityFilters) => {
      const conditions = [eq(activityLog.companyId, filters.companyId)];
@@ -27,6 +28,58 @@ export function activityService(db: Db) {
      return db.select().from(activityLog).where(and(...conditions)).orderBy(desc(activityLog.createdAt));
    },

+    forIssue: (issueId: string) =>
+      db
+        .select()
+        .from(activityLog)
+        .where(
+          and(
+            eq(activityLog.entityType, "issue"),
+            eq(activityLog.entityId, issueId),
+          ),
+        )
+        .orderBy(desc(activityLog.createdAt)),
+
+    runsForIssue: (issueId: string) =>
+      db
+        .selectDistinctOn([activityLog.runId], {
+          runId: activityLog.runId,
+          status: heartbeatRuns.status,
+          agentId: heartbeatRuns.agentId,
+          startedAt: heartbeatRuns.startedAt,
+          finishedAt: heartbeatRuns.finishedAt,
+          createdAt: heartbeatRuns.createdAt,
+          invocationSource: heartbeatRuns.invocationSource,
+        })
+        .from(activityLog)
+        .innerJoin(heartbeatRuns, eq(activityLog.runId, heartbeatRuns.id))
+        .where(
+          and(
+            eq(activityLog.entityType, "issue"),
+            eq(activityLog.entityId, issueId),
+            isNotNull(activityLog.runId),
+          ),
+        )
+        .orderBy(activityLog.runId, desc(heartbeatRuns.createdAt)),
+
+    issuesForRun: (runId: string) =>
+      db
+        .selectDistinctOn([issueIdAsText], {
+          issueId: issues.id,
+          title: issues.title,
+          status: issues.status,
+          priority: issues.priority,
+        })
+        .from(activityLog)
+        .innerJoin(issues, eq(activityLog.entityId, issueIdAsText))
+        .where(
+          and(
+            eq(activityLog.runId, runId),
+            eq(activityLog.entityType, "issue"),
+          ),
+        )
+        .orderBy(issueIdAsText),
+
    create: (data: typeof activityLog.$inferInsert) =>
      db
        .insert(activityLog)
--- a/server/src/services/heartbeat.ts
+++ b/server/src/services/heartbeat.ts
@@ -34,6 +34,10 @@ interface WakeupOptions {
  contextSnapshot?: Record<string, unknown>;
 }

+function readNonEmptyString(value: unknown): string | null {
+  return typeof value === "string" && value.trim().length > 0 ? value : null;
+}
+
 export function heartbeatService(db: Db) {
  const runLogStore = getRunLogStore();

@@ -216,6 +220,56 @@ export function heartbeatService(db: Db) {
    }
  }

+  async function reapOrphanedRuns(opts?: { staleThresholdMs?: number }) {
+    const staleThresholdMs = opts?.staleThresholdMs ?? 0;
+    const now = new Date();
+
+    // Find all runs in "queued" or "running" state
+    const activeRuns = await db
+      .select()
+      .from(heartbeatRuns)
+      .where(inArray(heartbeatRuns.status, ["queued", "running"]));
+
+    const reaped: string[] = [];
+
+    for (const run of activeRuns) {
+      if (runningProcesses.has(run.id)) continue;
+
+      // Apply staleness threshold to avoid false positives
+      if (staleThresholdMs > 0) {
+        const refTime = run.updatedAt ? new Date(run.updatedAt).getTime() : 0;
+        if (now.getTime() - refTime < staleThresholdMs) continue;
+      }
+
+      await setRunStatus(run.id, "failed", {
+        error: "Process lost -- server may have restarted",
+        errorCode: "process_lost",
+        finishedAt: now,
+      });
+      await setWakeupStatus(run.wakeupRequestId, "failed", {
+        finishedAt: now,
+        error: "Process lost -- server may have restarted",
+      });
+      const updatedRun = await getRun(run.id);
+      if (updatedRun) {
+        await appendRunEvent(updatedRun, 1, {
+          eventType: "lifecycle",
+          stream: "system",
+          level: "error",
+          message: "Process lost -- server may have restarted",
+        });
+      }
+      await finalizeAgentStatus(run.agentId, "failed");
+      runningProcesses.delete(run.id);
+      reaped.push(run.id);
+    }
+
+    if (reaped.length > 0) {
+      logger.warn({ reapedCount: reaped.length, runIds: reaped }, "reaped orphaned heartbeat runs");
+    }
+    return { reaped: reaped.length, runIds: reaped };
+  }
+
  async function updateRuntimeState(
    agent: typeof agents.$inferSelect,
    run: typeof heartbeatRuns.$inferSelect,
@@ -543,7 +597,26 @@ export function heartbeatService(db: Db) {
  async function enqueueWakeup(agentId: string, opts: WakeupOptions = {}) {
    const source = opts.source ?? "on_demand";
    const triggerDetail = opts.triggerDetail ?? null;
-    const contextSnapshot = opts.contextSnapshot ?? {};
+    const contextSnapshot: Record<string, unknown> = { ...(opts.contextSnapshot ?? {}) };
+    const reason = opts.reason ?? null;
+    const payload = opts.payload ?? null;
+    const issueIdFromPayload = readNonEmptyString(payload?.["issueId"]);
+
+    if (!readNonEmptyString(contextSnapshot["wakeReason"]) && reason) {
+      contextSnapshot.wakeReason = reason;
+    }
+    if (!readNonEmptyString(contextSnapshot["issueId"]) && issueIdFromPayload) {
+      contextSnapshot.issueId = issueIdFromPayload;
+    }
+    if (!readNonEmptyString(contextSnapshot["taskId"]) && issueIdFromPayload) {
+      contextSnapshot.taskId = issueIdFromPayload;
+    }
+    if (!readNonEmptyString(contextSnapshot["wakeSource"])) {
+      contextSnapshot.wakeSource = source;
+    }
+    if (!readNonEmptyString(contextSnapshot["wakeTriggerDetail"]) && triggerDetail) {
+      contextSnapshot.wakeTriggerDetail = triggerDetail;
+    }

    const agent = await getAgent(agentId);
    if (!agent) throw notFound("Agent not found");
@@ -560,7 +633,7 @@ export function heartbeatService(db: Db) {
        source,
        triggerDetail,
        reason,
-        payload: opts.payload ?? null,
+        payload,
        status: "skipped",
        requestedByActorType: opts.requestedByActorType ?? null,
        requestedByActorId: opts.requestedByActorId ?? null,
@@ -591,8 +664,8 @@ export function heartbeatService(db: Db) {
        agentId,
        source,
        triggerDetail,
-        reason: opts.reason ?? null,
-        payload: opts.payload ?? null,
+        reason,
+        payload,
        status: "coalesced",
        coalescedCount: 1,
        requestedByActorType: opts.requestedByActorType ?? null,
@@ -611,8 +684,8 @@ export function heartbeatService(db: Db) {
        agentId,
        source,
        triggerDetail,
-        reason: opts.reason ?? null,
-        payload: opts.payload ?? null,
+        reason,
+        payload,
        status: "queued",
        requestedByActorType: opts.requestedByActorType ?? null,
        requestedByActorId: opts.requestedByActorId ?? null,
@@ -757,6 +830,8 @@ export function heartbeatService(db: Db) {

    wakeup: enqueueWakeup,

+    reapOrphanedRuns,
+
    tickTimers: async (now = new Date()) => {
      const allAgents = await db.select().from(agents);
      let checked = 0;
@@ -860,5 +935,20 @@ export function heartbeatService(db: Db) {

      return runs.length;
    },
+
+    getActiveRunForAgent: async (agentId: string) => {
+      const [run] = await db
+        .select()
+        .from(heartbeatRuns)
+        .where(
+          and(
+            eq(heartbeatRuns.agentId, agentId),
+            eq(heartbeatRuns.status, "running"),
+          ),
+        )
+        .orderBy(desc(heartbeatRuns.startedAt))
+        .limit(1);
+      return run ?? null;
+    },
  };
 }
--- a/server/src/services/issues.ts
+++ b/server/src/services/issues.ts
@@ -1,6 +1,6 @@
 import { and, asc, desc, eq, inArray, isNull, or, sql } from "drizzle-orm";
 import type { Db } from "@paperclip/db";
-import { agents, issues, issueComments } from "@paperclip/db";
+import { agents, companies, issues, issueComments } from "@paperclip/db";
 import { conflict, notFound, unprocessable } from "../errors.js";

 const ISSUE_TRANSITIONS: Record<string, string[]> = {
@@ -9,8 +9,8 @@ const ISSUE_TRANSITIONS: Record<string, string[]> = {
  in_progress: ["in_review", "blocked", "done", "cancelled"],
  in_review: ["in_progress", "done", "cancelled"],
  blocked: ["todo", "in_progress", "cancelled"],
-  done: [],
-  cancelled: [],
+  done: ["todo"],
+  cancelled: ["todo"],
 };

 function assertTransition(from: string, to: string) {
@@ -69,23 +69,38 @@ export function issueService(db: Db) {
        .where(eq(issues.id, id))
        .then((rows) => rows[0] ?? null),

-    create: (companyId: string, data: Omit<typeof issues.$inferInsert, "companyId">) => {
-      const values = { ...data, companyId } as typeof issues.$inferInsert;
-      if (values.status === "in_progress" && !values.startedAt) {
-        values.startedAt = new Date();
-      }
-      if (values.status === "done") {
-        values.completedAt = new Date();
-      }
-      if (values.status === "cancelled") {
-        values.cancelledAt = new Date();
-      }
+    getByIdentifier: (identifier: string) =>
+      db
+        .select()
+        .from(issues)
+        .where(eq(issues.identifier, identifier.toUpperCase()))
+        .then((rows) => rows[0] ?? null),

-      return db
-        .insert(issues)
-        .values(values)
-        .returning()
-        .then((rows) => rows[0]);
+    create: async (companyId: string, data: Omit<typeof issues.$inferInsert, "companyId">) => {
+      return db.transaction(async (tx) => {
+        const [company] = await tx
+          .update(companies)
+          .set({ issueCounter: sql`${companies.issueCounter} + 1` })
+          .where(eq(companies.id, companyId))
+          .returning({ issueCounter: companies.issueCounter, issuePrefix: companies.issuePrefix });
+
+        const issueNumber = company.issueCounter;
+        const identifier = `${company.issuePrefix}-${issueNumber}`;
+
+        const values = { ...data, companyId, issueNumber, identifier } as typeof issues.$inferInsert;
+        if (values.status === "in_progress" && !values.startedAt) {
+          values.startedAt = new Date();
+        }
+        if (values.status === "done") {
+          values.completedAt = new Date();
+        }
+        if (values.status === "cancelled") {
+          values.cancelledAt = new Date();
+        }
+
+        const [issue] = await tx.insert(issues).values(values).returning();
+        return issue;
+      });
    },

    update: async (id: string, data: Partial<typeof issues.$inferInsert>) => {
@@ -110,6 +125,12 @@ export function issueService(db: Db) {
      }

      applyStatusSideEffects(data.status, patch);
+      if (data.status && data.status !== "done") {
+        patch.completedAt = null;
+      }
+      if (data.status && data.status !== "cancelled") {
+        patch.cancelledAt = null;
+      }

      return db
        .update(issues)
--- a/server/src/types/express.d.ts
+++ b/server/src/types/express.d.ts
@@ -9,6 +9,7 @@ declare global {
        agentId?: string;
        companyId?: string;
        keyId?: string;
+        runId?: string;
      };
    }
  }