Dispatch scheduled work from saved deadlines

Routine and issue-monitor work can wait for a heartbeat scan even when
the app wakes before a saved deadline. Register independent deadline
workers with the existing delivery coordinator and notify them after
producer transactions settle. Preserve the interval recovery scan,
execution checks, atomic claims, and idle/standby/shutdown gates.

Parse each cron expression once per next-run search to avoid repeating
that work for every minute of a sparse schedule.

Verified focused scheduler, routine, SQL eligibility, and notification
tests, workspace typecheck, and full build. Full-suite and real local
dispatch acceptance are tracked in the PR before final readiness.

Co-Authored-By: Paperclip <noreply@paperclip.ing>

doc/DEVELOPING.md

@@ -1448,6 +1448,18 @@ When a workspace service runs Paperclip for browser OAuth QA, configure its `exp
 
 ## Heartbeat Service Extractions
 
+Routine and issue-monitor dispatch uses saved future deadlines through
+`server/src/services/scheduled-work.ts` and the existing delivery coordinator.
+Startup restores the next deadline. Routine edits and monitor changes notify
+their worker after the enclosing database transaction settles. Each worker runs
+independently and retains the existing atomic claims and execution checks.
+The heartbeat interval still requests a recovery scan; it does not determine
+the dispatch time of a known future deadline. Failed scans retry at that same
+interval. Future timers do not hold idle work open, and standby, idle drain and
+shutdown retain the coordinator's admission gates. External database writers
+rely on the periodic recovery scan. Sparse cron searches reuse one parsed
+expression so repeated parsing cannot block unrelated deadlines.
+
 Keep relevant heartbeat extractions and their focused tests in `server/src/services/heartbeat/`.
 Follow [Heartbeat execution boundaries](../rules/heartbeat-execution-boundaries.mdc)
 for state lifetime, admission, recovery ownership, cleanup ordering, and verification.

server/src/__tests__/routines-service.test.ts

@@ -1,3 +1,5 @@
+import { subscribeDatabaseWork } from "@paperclipai/db";
+import { DELIVERY_QUEUES } from "../services/delivery-work-notifications.js";
 import { createHmac, randomUUID } from "node:crypto";
 import { eq } from "drizzle-orm";
 import { afterAll, afterEach, beforeAll, describe, expect, it, vi } from "vitest";
@@ -214,6 +216,40 @@ describeEmbeddedPostgres("routine service live-execution coalescing", () => {
     return { companyId, agentId, issueSvc, projectId, routine, svc, wakeups };
   }
 
+  it("notifies scheduled routine work after trigger transactions settle", async () => {
+    const f = await seedFixture();
+    const events: string[] = [];
+    const unsubscribe = subscribeDatabaseWork(db, DELIVERY_QUEUES.routineSchedules, event => { events.push(event); });
+    try {
+      const created = await f.svc.createTrigger(f.routine.id,
+        { kind: "schedule", cronExpression: "0 * * * *", timezone: "UTC" }, {});
+      expect(events).toEqual(["intent", "settled"]);
+      events.length = 0;
+      await f.svc.updateTrigger(created.trigger.id, { cronExpression: "30 * * * *" }, {});
+      expect(events).toEqual(["intent", "settled"]);
+      events.length = 0;
+      await f.svc.deleteTrigger(created.trigger.id, {});
+      expect(events).toEqual(["intent", "settled"]);
+    } finally { unsubscribe(); }
+  });
+
+  it("notifies monitor work when an issue deadline is created and changed", async () => {
+    const f = await seedFixture();
+    const events: string[] = [];
+    const unsubscribe = subscribeDatabaseWork(db, DELIVERY_QUEUES.issueMonitors, event => { events.push(event); });
+    const next = new Date(Date.now() + 600_000);
+    try {
+      const issue = await f.issueSvc.create(f.companyId, {
+        title: "Scheduled check", status: "in_progress", assigneeAgentId: f.agentId,
+        executionPolicy: { mode: "normal", commentRequired: true, stages: [], monitor: { nextCheckAt: next.toISOString() } },
+      });
+      expect(events).toEqual(["intent", "settled"]);
+      events.length = 0;
+      await f.issueSvc.update(issue.id, { monitorNextCheckAt: new Date(next.getTime() + 60_000) });
+      expect(events).toEqual(["intent", "settled"]);
+    } finally { unsubscribe(); }
+  });
+
   async function armWorktreeExecution(cutoff: Date, instanceId = "worktree-routines-test") {
     await db.insert(instanceSettings).values({
       singletonKey: "default",

server/src/__tests__/scheduled-work-postgres.test.ts

@@ -0,0 +1,65 @@
+import { agents, companies, createDb, issues, routines, routineTriggers } from "@paperclipai/db";
+import { sql } from "drizzle-orm";
+import type { Db } from "@paperclipai/db";
+import { afterAll, beforeAll, describe, expect, it } from "vitest";
+import { getEmbeddedPostgresTestSupport, startEmbeddedPostgresTestDatabase } from "./helpers/embedded-postgres.js";
+import type { createDeliveryWorkCoordinator } from "../services/delivery-work-coordinator.js";
+import { DELIVERY_QUEUES, type DeliveryQueue } from "../services/delivery-work-notifications.js";
+import { registerScheduledWork } from "../services/scheduled-work.js";
+
+const support = await getEmbeddedPostgresTestSupport();
+describe.skipIf(!support.supported)("scheduled deadline database queries", () => {
+  let database: Awaited<ReturnType<typeof startEmbeddedPostgresTestDatabase>>;
+  let db: Db;
+  beforeAll(async () => {
+    database = await startEmbeddedPostgresTestDatabase("paperclip-scheduled-deadlines");
+    db = createDb(database.connectionString);
+  }, 30_000);
+  afterAll(async () => { await db?.$client.end(); await database?.cleanup(); });
+
+  it("selects future eligible deadlines and excludes inactive, mismatched and past work", async () => {
+    const now = Date.now();
+    const at = (minutes: number) => new Date(now + minutes * 60_000);
+    const [company, pausedCompany] = await db.insert(companies).values([
+      { name: "Active schedules", issuePrefix: "SCH" },
+      { name: "Paused schedules", issuePrefix: "PAU", status: "paused" },
+    ]).returning();
+    const [agent] = await db.insert(agents).values({ companyId: company!.id, name: "Scheduled agent" }).returning();
+    const [active, paused, otherCompany] = await db.insert(routines).values([
+      { companyId: company!.id, title: "Active routine" },
+      { companyId: company!.id, title: "Paused routine", status: "paused" },
+      { companyId: pausedCompany!.id, title: "Paused company routine" },
+    ]).returning();
+    const trigger = { companyId: company!.id, routineId: active!.id, kind: "schedule" };
+    await db.insert(routineTriggers).values([
+      { ...trigger, nextRunAt: at(10) },
+      { ...trigger, enabled: false, nextRunAt: at(1) },
+      { ...trigger, archived: true, nextRunAt: at(2) },
+      { ...trigger, routineId: paused!.id, nextRunAt: at(3) },
+      { ...trigger, companyId: pausedCompany!.id, nextRunAt: at(4) },
+      { ...trigger, companyId: pausedCompany!.id, routineId: otherCompany!.id, nextRunAt: at(5) },
+      { ...trigger, nextRunAt: at(-1) },
+    ]);
+    const monitor = { companyId: company!.id, title: "Monitor", status: "in_progress", assigneeAgentId: agent!.id };
+    await db.insert(issues).values([
+      { ...monitor, monitorNextCheckAt: at(15) },
+      { ...monitor, status: "done", monitorNextCheckAt: at(1) },
+      { ...monitor, assigneeUserId: "fixture-user", monitorNextCheckAt: at(2) },
+      { ...monitor, assigneeAgentId: null, monitorNextCheckAt: at(3) },
+      { ...monitor, companyId: pausedCompany!.id, monitorNextCheckAt: at(4) },
+      { ...monitor, monitorNextCheckAt: at(-1) },
+    ]);
+    type Task = Parameters<ReturnType<typeof createDeliveryWorkCoordinator>["register"]>[1];
+    const tasks = new Map<DeliveryQueue, Task>();
+    registerScheduledWork({ register: (queue, task) => {
+      tasks.set(queue, task);
+      return { ready: Promise.resolve(), wake: () => {} };
+    } }, db, { retryMs: 60_000, tickTimers: async () => {}, tickRoutines: async () => {} });
+    for (const task of tasks.values()) await task.run(new AbortController().signal);
+    expect(tasks.get(DELIVERY_QUEUES.routineSchedules)!.nextRunAt!()).toBe(at(10).getTime());
+    expect(tasks.get(DELIVERY_QUEUES.issueMonitors)!.nextRunAt!()).toBe(at(15).getTime());
+    await db.execute(sql`truncate table companies restart identity cascade`);
+    for (const task of tasks.values()) await task.run(new AbortController().signal);
+    for (const task of tasks.values()) expect(task.nextRunAt!()).toBeNull();
+  });
+});

server/src/__tests__/scheduled-work.test.ts

@@ -0,0 +1,132 @@
+import { PgDialect } from "drizzle-orm/pg-core";
+import type { Db } from "@paperclipai/db";
+import { installDatabaseWorkSignals } from "../../../packages/db/src/work-signals.js";
+import { afterEach, describe, expect, it, vi } from "vitest";
+import { createDeliveryWorkCoordinator } from "../services/delivery-work-coordinator.js";
+import { DELIVERY_QUEUES, notifyDeliveryWork } from "../services/delivery-work-notifications.js";
+import { registerScheduledWork } from "../services/scheduled-work.js";
+import { idleWorkSnapshot } from "../services/task-admission.js";
+
+const coordinators: ReturnType<typeof createDeliveryWorkCoordinator>[] = [];
+afterEach(async () => {
+  for (const coordinator of coordinators.splice(0)) await coordinator.stop();
+  vi.useRealTimers();
+});
+
+function fixture(input: { routine?: number | null; monitor?: number | null; tickRoutines?: () => Promise<void> } = {}) {
+  vi.useFakeTimers();
+  vi.setSystemTime(new Date("2020-01-01T00:00:00.000Z"));
+  const dialect = new PgDialect();
+  const deadlines = { routine: input.routine ?? null, monitor: input.monitor ?? null };
+  let canRun = true;
+  let failRead = false;
+  const execute = vi.fn(async (query: any) => {
+    const text = dialect.sqlToQuery(query).sql;
+    if (text.includes("pg_current_xact_id")) return [{ xid: "42" }];
+    if (failRead) throw new Error("database unavailable");
+    const at = deadlines[text.includes("routine_triggers") ? "routine" : "monitor"];
+    return [{ next_at: at !== null && at > Date.now() ? new Date(at) : null }];
+  });
+  const owner = installDatabaseWorkSignals({ execute, async transaction(callback: (tx: any) => Promise<any>) {
+    return callback({ execute, transaction: owner.transaction });
+  } });
+  const errors = vi.fn();
+  const coordinator = createDeliveryWorkCoordinator({ owner, canRun: () => canRun, onError: errors });
+  coordinators.push(coordinator);
+  const tickTimers = vi.fn(async () => {});
+  const tickRoutines = vi.fn(input.tickRoutines ?? (async () => {}));
+  const workers = registerScheduledWork(coordinator, owner as unknown as Db,
+    { retryMs: 60_000, tickTimers, tickRoutines });
+  return { coordinator, workers, owner, deadlines, execute, tickTimers, tickRoutines, errors,
+    ready: () => Promise.all([workers.routines.ready, workers.timers.ready]),
+    canRun: (value: boolean) => { canRun = value; }, failRead: (value: boolean) => { failRead = value; } };
+}
+
+describe("scheduled routine and monitor deadlines", () => {
+  it("dispatches at each saved deadline without waiting for a periodic tick", async () => {
+    const now = Date.UTC(2020, 0, 1);
+    const f = fixture({ routine: now + 10_000, monitor: now + 20_000 });
+    await f.ready();
+    expect(f.coordinator.nextWakeAt()).toBe(now + 10_000);
+    expect(idleWorkSnapshot().active).toBe(0);
+    await vi.advanceTimersByTimeAsync(9999);
+    expect(f.tickRoutines).toHaveBeenCalledTimes(1);
+    await vi.advanceTimersByTimeAsync(1);
+    expect(f.tickRoutines).toHaveBeenCalledTimes(2);
+    expect(f.tickTimers).toHaveBeenCalledTimes(1);
+    expect(f.coordinator.nextWakeAt()).toBe(now + 20_000);
+    await vi.advanceTimersByTimeAsync(10_000);
+    expect(f.tickTimers).toHaveBeenCalledTimes(2);
+    expect(f.coordinator.nextWakeAt()).toBeNull();
+    expect(f.execute).toHaveBeenCalledTimes(4);
+    expect(idleWorkSnapshot().active).toBe(0);
+    await vi.advanceTimersByTimeAsync(3_600_000);
+    expect(f.execute).toHaveBeenCalledTimes(4);
+  });
+
+  it("rearms an earlier deadline only after the producer transaction settles", async () => {
+    const now = Date.UTC(2020, 0, 1);
+    const f = fixture({ routine: now + 600_000 });
+    await f.ready();
+    let commit!: () => void;
+    const held = new Promise<void>(resolve => { commit = resolve; });
+    const writing = f.owner.transaction(async tx => {
+      await notifyDeliveryWork(tx, DELIVERY_QUEUES.routineSchedules);
+      f.deadlines.routine = now + 10_000;
+      await held;
+    });
+    try {
+      await vi.advanceTimersByTimeAsync(1000);
+      expect(f.tickRoutines).toHaveBeenCalledTimes(1);
+      expect(idleWorkSnapshot().active).toBe(1);
+    } finally { commit(); await writing; }
+    await vi.advanceTimersByTimeAsync(1);
+    expect(f.coordinator.nextWakeAt()).toBe(now + 10_000);
+    expect(idleWorkSnapshot().active).toBe(0);
+    await vi.advanceTimersByTimeAsync(8999);
+    expect(f.tickRoutines).toHaveBeenCalledTimes(3);
+    expect(f.tickTimers).toHaveBeenCalledTimes(1);
+  });
+
+  it("keeps monitor dispatch responsive while routine work is slow", async () => {
+    let release!: () => void;
+    const held = new Promise<void>(resolve => { release = resolve; });
+    const f = fixture({ monitor: Date.UTC(2020, 0, 1) + 10_000, tickRoutines: () => held });
+    try {
+      await f.workers.timers.ready;
+      await vi.advanceTimersByTimeAsync(10_000);
+      expect(f.tickTimers).toHaveBeenCalledTimes(2);
+      expect(f.tickRoutines).toHaveBeenCalledTimes(1);
+    } finally { release(); await f.workers.routines.ready; }
+  });
+
+  it("does not dispatch during idle drain or standby and cancels deadlines on stop", async () => {
+    const f = fixture({ routine: Date.UTC(2020, 0, 1) + 10_000 });
+    await f.ready();
+    f.canRun(false);
+    await vi.advanceTimersByTimeAsync(10_000);
+    expect(f.tickRoutines).toHaveBeenCalledTimes(1);
+    expect(idleWorkSnapshot().active).toBe(0);
+    await f.coordinator.stop();
+    f.canRun(true);
+    await vi.advanceTimersByTimeAsync(3_600_000);
+    expect(f.tickRoutines).toHaveBeenCalledTimes(1);
+    expect(vi.getTimerCount()).toBe(0);
+  });
+
+  it("retries failed deadline reads at the fallback interval without a tight loop", async () => {
+    const f = fixture();
+    await f.ready();
+    f.failRead(true);
+    f.workers.routines.wake();
+    await vi.advanceTimersByTimeAsync(1);
+    expect(f.errors).toHaveBeenCalledTimes(1);
+    await vi.advanceTimersByTimeAsync(59_000);
+    expect(f.tickRoutines).toHaveBeenCalledTimes(2);
+    f.failRead(false);
+    await vi.advanceTimersByTimeAsync(1000);
+    expect(f.tickRoutines).toHaveBeenCalledTimes(3);
+    expect(f.coordinator.nextWakeAt()).toBeNull();
+    expect(idleWorkSnapshot().active).toBe(0);
+  });
+});

server/src/index.ts

@@ -7,6 +7,7 @@ import {
 } from "./services/skill-version-retention.js";
 import { subscribeAllCompanyLiveEvents } from "./services/live-events.js";
 import { DELIVERY_QUEUES } from "./services/delivery-work-notifications.js";
+import { registerScheduledWork } from "./services/scheduled-work.js";
 import type { createDeliveryWorkCoordinator } from "./services/delivery-work-coordinator.js";
 import { registerTerminalWorkspaceWork, TERMINAL_WORKSPACE_RETRY_MS } from "./services/terminal-workspace-work.js";
 import { isIdleTaskDrainActive, beginIdleTrackedWork, trackIdleWork } from "./services/task-admission.js";
@@ -1718,7 +1719,7 @@ async function startServerWithDatabaseTeardown(
       await step("retention_sweep", runRetentionSweep);
     };
 
-    const startHeartbeatScheduler = () => startHeartbeatSchedulerInterval(() => {
+    const createHeartbeatSchedulerTick = (scheduled: ReturnType<typeof registerScheduledWork>) => () => {
       // Track the outer async callback as well as the work it starts. Shutdown
       // can then wait through an already-running suppression check before it
       // captures the authoritative set of running heartbeat rows.
@@ -1738,18 +1739,7 @@ async function startServerWithDatabaseTeardown(
           );
         }
 
-        if (!(await heartbeat.resolveSchedulingSuppression()).suppressed) {
-          trackHeartbeatSchedulerWork(heartbeat
-            .tickTimers(new Date())
-            .then((result) => {
-              if (result.enqueued > 0) {
-                logger.info({ ...result }, "heartbeat timer tick enqueued runs");
-              }
-            })
-            .catch((err) => {
-              logger.error({ err }, "heartbeat timer tick failed");
-            }));
-        }
+        scheduled.timers.wake();
 
         if (isIdleTaskDrainActive() || heartbeatSchedulerStopped) return;
         scheduleExternalObjectRefreshSweep(new Date());
@@ -1763,16 +1753,7 @@ async function startServerWithDatabaseTeardown(
         scheduleEnvironmentLeaseCleanupSweep();
 
         if (isIdleTaskDrainActive() || heartbeatSchedulerStopped) return;
-        trackHeartbeatSchedulerWork(routines
-          .tickScheduledTriggers(new Date())
-          .then((result) => {
-            if (result.triggered > 0) {
-              logger.info({ ...result }, "routine scheduler tick enqueued runs");
-            }
-          })
-          .catch((err) => {
-            logger.error({ err }, "routine scheduler tick failed");
-          }));
+        scheduled.routines.wake();
 
         if (isIdleTaskDrainActive() || heartbeatSchedulerStopped) return;
         trackHeartbeatSchedulerWork((async () => {
@@ -1896,7 +1877,20 @@ async function startServerWithDatabaseTeardown(
       })().catch((err) => {
         logger.error({ err }, "heartbeat scheduler tick failed");
       }));
-    });
+    };
+    const startHeartbeatScheduler = () => {
+      const scheduled = registerScheduledWork(deliveryWork, db, {
+        retryMs: config.heartbeatSchedulerIntervalMs,
+        tickTimers: () => heartbeat.tickTimers(new Date()).then(result => {
+          if (result.enqueued > 0) logger.info({ ...result }, "heartbeat timer tick enqueued runs");
+        }),
+        tickRoutines: () => routines.tickScheduledTriggers(new Date()).then(result => {
+          if (result.triggered > 0) logger.info({ ...result }, "routine scheduler tick enqueued runs");
+        }),
+      });
+      trackHeartbeatSchedulerWork(Promise.all([scheduled.timers.ready, scheduled.routines.ready]));
+      startHeartbeatSchedulerInterval(createHeartbeatSchedulerTick(scheduled));
+    };
     trackHeartbeatSchedulerWork(runStartupHousekeeping().then(() => {
       if (!heartbeatSchedulerStopped) startHeartbeatScheduler();
     }));

server/src/services/delivery-work-notifications.ts

@@ -27,6 +27,8 @@ export const DELIVERY_QUEUES = {
   pluginLifecycle: "plugin-resource-lifecycle",
   toolAction: "tool-action-receipts",
   terminalWorkspaces: "terminal-workspaces",
+  routineSchedules: "routine-schedules",
+  issueMonitors: "issue-monitors",
 } as const;
 export type DeliveryQueue = typeof DELIVERY_QUEUES[keyof typeof DELIVERY_QUEUES];
 

server/src/services/issues.ts

@@ -9,6 +9,7 @@ import { type TaskWorkspaceSelection, type TaskWorkspaceIntent } from "@papercli
 import { executionWorkspaceService } from "./execution-workspaces.js";
 import { notifyChatPublicationWork } from "./chat-work-notifications.js";
 import { notifyTerminalWorkspaceWork } from "./terminal-workspace-work.js";
+import { DELIVERY_QUEUES, notifyDeliveryWork } from "./delivery-work-notifications.js";
 import { recordChatHandoff, recordChatCompletion, existingChatCompletionReply, acknowledgeChatCompletionReply } from "./chat-completion-delivery.js";
 import { mirrorSlackBoardComment, slackBoardReplyBindings } from "./slack-board-messages.js";
 import { assertAgentRunWriteAllowed } from "../agent-run-cancellation.js";
@@ -10383,6 +10384,7 @@ export function issueService(db: Db) {
           await notifyTerminalWorkspaceWork(tx, values.executionWorkspaceId ? `workspace:${values.executionWorkspaceId}`
             : values.parentId ? `issue:${values.parentId}` : undefined);
         }
+        if (values.monitorNextCheckAt) await notifyDeliveryWork(tx, DELIVERY_QUEUES.issueMonitors);
         const [issue] = await tx.insert(issues).values(values).returning();
         await attachOwnedDraftImages(tx, issue, issue.description, { userId: issueData.createdByUserId, agentId: issueData.createdByAgentId });
         if (issue.visibility === "private" && !inheritedPrivateSubtree && issueData.createdByAgentId) {
@@ -11205,6 +11207,10 @@ export function issueService(db: Db) {
           || issueData.parentId !== undefined || issueData.executionWorkspaceId !== undefined) {
           await notifyTerminalWorkspaceWork(tx, `issue:${id}`);
         }
+        if (patch.monitorNextCheckAt !== undefined || (receiptExisting.monitorNextCheckAt &&
+          (patch.status !== undefined || patch.assigneeAgentId !== undefined || patch.assigneeUserId !== undefined))) {
+          await notifyDeliveryWork(tx, DELIVERY_QUEUES.issueMonitors);
+        }
         const updated = await tx
           .update(issues)
           .set(patch)

server/src/services/routines-formatter-cache.test.ts

@@ -1,11 +1,25 @@
 import { afterEach, describe, expect, it, vi } from "vitest";
 import { nextCronTickInTimeZone } from "./routines.js";
+import * as cron from "./cron.js";
 
 describe("nextCronTickInTimeZone formatter caching", () => {
   afterEach(() => {
     vi.restoreAllMocks();
   });
 
+  it("parses a sparse schedule once instead of once per searched minute", () => {
+    const parse = cron.parseCron;
+    let parses = 0;
+    vi.spyOn(cron, "parseCron").mockImplementation(expression => {
+      parses++;
+      if (parses > 1) throw new Error("Repeated cron parsing blocks unrelated scheduled work");
+      return parse(expression);
+    });
+    const next = nextCronTickInTimeZone("0 12 1 1 *", "UTC", new Date("2020-01-01T12:00:00Z"));
+    expect(next?.toISOString()).toBe("2021-01-01T12:00:00.000Z");
+    expect(parses).toBe(1);
+  });
+
   it("computes the next occurrence of a sparse monthly cron correctly", () => {
     const next = nextCronTickInTimeZone(
       "30 6 1 * *",

server/src/services/routines.ts

@@ -1,3 +1,4 @@
+import { DELIVERY_QUEUES, notifyDeliveryWork } from "./delivery-work-notifications.js";
 import { verifyAppWebhook } from "./app-webhook.js";
 import crypto from "node:crypto";
 import { verifyFirefliesWebhook } from "./fireflies-webhook.js";
@@ -253,8 +254,7 @@ function getZonedMinuteParts(date: Date, timeZone: string) {
   };
 }
 
-function matchesCronMinute(expression: string, timeZone: string, date: Date) {
-  const cron = parseCron(expression);
+function matchesCronMinute(cron: ReturnType<typeof parseCron>, timeZone: string, date: Date) {
   const parts = getZonedMinuteParts(date, timeZone);
   return (
     cron.minutes.includes(parts.minute) &&
@@ -268,16 +268,18 @@ function matchesCronMinute(expression: string, timeZone: string, date: Date) {
 export function nextCronTickInTimeZone(expression: string, timeZone: string, after: Date) {
   const trimmed = expression.trim();
   assertTimeZone(timeZone);
-  const error = validateCron(trimmed);
-  if (error) {
-    throw unprocessable(error);
+  let cron: ReturnType<typeof parseCron>;
+  try {
+    cron = parseCron(trimmed);
+  } catch (error) {
+    throw unprocessable(error instanceof Error ? error.message : String(error));
   }
 
   const cursor = floorToMinute(after);
   cursor.setUTCMinutes(cursor.getUTCMinutes() + 1);
   const limit = 366 * 24 * 60 * 5;
   for (let i = 0; i < limit; i += 1) {
-    if (matchesCronMinute(trimmed, timeZone, cursor)) {
+    if (matchesCronMinute(cron, timeZone, cursor)) {
       return new Date(cursor.getTime());
     }
     cursor.setUTCMinutes(cursor.getUTCMinutes() + 1);
@@ -2230,6 +2232,7 @@ export function routineService(
       }
       const createdRoutine = await db.transaction(async (tx) => {
         const txDb = tx as unknown as Db;
+        await notifyDeliveryWork(txDb, DELIVERY_QUEUES.routineSchedules);
         const [created] = await txDb
           .insert(routines)
           .values({
@@ -2334,6 +2337,7 @@ export function routineService(
       }
       const updatedRoutine = await db.transaction(async (tx) => {
         const txDb = tx as unknown as Db;
+        await notifyDeliveryWork(txDb, DELIVERY_QUEUES.routineSchedules);
         await tx.execute(sql`select id from ${routines} where ${routines.id} = ${id} for update`);
         const locked = await txDb
           .select()
@@ -2488,6 +2492,7 @@ export function routineService(
 
       const { trigger, revision } = await db.transaction(async (tx) => {
         const txDb = tx as unknown as Db;
+        await notifyDeliveryWork(txDb, DELIVERY_QUEUES.routineSchedules);
         await tx.execute(sql`select id from ${routines} where ${routines.id} = ${routine.id} for update`);
         const [createdTrigger] = await txDb
           .insert(routineTriggers)
@@ -2562,6 +2567,7 @@ export function routineService(
 
       const result = await db.transaction(async (tx) => {
         const txDb = tx as unknown as Db;
+        await notifyDeliveryWork(txDb, DELIVERY_QUEUES.routineSchedules);
         await tx.execute(sql`select id from ${routines} where ${routines.id} = ${existing.routineId} for update`);
         const [updated] = await txDb
           .update(routineTriggers)
@@ -2601,6 +2607,7 @@ export function routineService(
       if (!existing) return { deleted: false, revision: null };
       const result = await db.transaction(async (tx) => {
         const txDb = tx as unknown as Db;
+        await notifyDeliveryWork(txDb, DELIVERY_QUEUES.routineSchedules);
         await tx.execute(sql`select id from ${routines} where ${routines.id} = ${existing.routineId} for update`);
         await txDb.delete(routineTriggers).where(eq(routineTriggers.id, id));
         const routine = await txDb
@@ -2719,6 +2726,7 @@ export function routineService(
 
       const result = await db.transaction(async (tx) => {
         const txDb = tx as unknown as Db;
+        await notifyDeliveryWork(txDb, DELIVERY_QUEUES.routineSchedules);
         await tx.execute(sql`select id from ${routines} where ${routines.id} = ${existingRoutine.id} for update`);
         const locked = await txDb
           .select()

server/src/services/scheduled-work.ts

@@ -0,0 +1,45 @@
+import type { Db } from "@paperclipai/db";
+import { sql, type SQL } from "drizzle-orm";
+import type { createDeliveryWorkCoordinator } from "./delivery-work-coordinator.js";
+import { DELIVERY_QUEUES, type DeliveryQueue } from "./delivery-work-notifications.js";
+
+export function registerScheduledWork(
+  coordinator: Pick<ReturnType<typeof createDeliveryWorkCoordinator>, "register">,
+  db: Pick<Db, "execute">,
+  options: {
+    retryMs: number;
+    tickTimers: () => Promise<unknown>;
+    tickRoutines: () => Promise<unknown>;
+  },
+) {
+  function register(queue: DeliveryQueue, work: () => Promise<unknown>, query: (now: Date) => SQL) {
+    let next: number | null = null;
+    return coordinator.register(queue, {
+      retryMs: options.retryMs,
+      run: async () => {
+        await work();
+        const [row] = await db.execute<{ next_at: Date | string | null }>(query(new Date()));
+        if (!row || row.next_at === undefined) throw new Error("Scheduled deadline query returned no result");
+        next = row.next_at === null ? null
+          : row.next_at instanceof Date ? row.next_at.getTime() : Date.parse(row.next_at);
+        if (next !== null && !Number.isFinite(next)) throw new Error("Scheduled deadline is invalid");
+      },
+      hasPending: async () => false,
+      nextRunAt: () => next,
+    });
+  }
+
+  const routines = register(DELIVERY_QUEUES.routineSchedules, options.tickRoutines, now => sql`
+    SELECT min(t.next_run_at) AS next_at
+    FROM routine_triggers t JOIN routines r ON r.id = t.routine_id AND r.company_id = t.company_id
+    JOIN companies c ON c.id = r.company_id
+    WHERE t.kind = 'schedule' AND t.enabled AND NOT t.archived
+      AND r.status = 'active' AND c.status = 'active' AND t.next_run_at > ${now.toISOString()}::timestamptz`);
+  const timers = register(DELIVERY_QUEUES.issueMonitors, options.tickTimers, now => sql`
+    SELECT min(i.monitor_next_check_at) AS next_at
+    FROM issues i JOIN companies c ON c.id = i.company_id
+    WHERE c.status = 'active' AND i.status IN ('in_progress', 'in_review')
+      AND i.assignee_agent_id IS NOT NULL AND i.assignee_user_id IS NULL
+      AND i.monitor_next_check_at > ${now.toISOString()}::timestamptz`);
+  return { routines, timers };
+}