fix(cron): skip stale delayed deliveries

tyler6204 · tyler6204 · commit fa2d38e23951 · 2026-03-18T17:18:37.000-07:00
diff --git a/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts b/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
@@ -143,6 +143,7 @@ describe("dispatchCronDelivery — double-announce guard", () => {
   });
 
   afterEach(() => {
+    vi.useRealTimers();
     vi.unstubAllEnvs();
   });
 
@@ -255,6 +256,39 @@ describe("dispatchCronDelivery — double-announce guard", () => {
     ).toBe(false);
   });
 
+  it("skips stale cron deliveries while still suppressing fallback main summary", async () => {
+    vi.useFakeTimers();
+    vi.setSystemTime(new Date("2026-03-18T17:00:00.000Z"));
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({ synthesizedText: "Yesterday's morning briefing." });
+    (params.job as { state?: { nextRunAtMs?: number } }).state = {
+      nextRunAtMs: Date.now() - (3 * 60 * 60_000 + 1),
+    };
+
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.result).toEqual(
+      expect.objectContaining({
+        status: "ok",
+        delivered: false,
+        deliveryAttempted: true,
+      }),
+    );
+    expect(deliverOutboundPayloads).not.toHaveBeenCalled();
+    expect(
+      shouldEnqueueCronMainSummary({
+        summaryText: "Yesterday's morning briefing.",
+        deliveryRequested: true,
+        delivered: state.result?.delivered,
+        deliveryAttempted: state.result?.deliveryAttempted,
+        suppressMainSummary: false,
+        isCronSystemEvent: () => true,
+      }),
+    ).toBe(false);
+  });
+
   it("text delivery fires exactly once (no double-deliver)", async () => {
     vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
     vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
diff --git a/src/cron/isolated-agent/delivery-dispatch.ts b/src/cron/isolated-agent/delivery-dispatch.ts
@@ -134,6 +134,8 @@ const PERMANENT_DIRECT_CRON_DELIVERY_ERROR_PATTERNS: readonly RegExp[] = [
   /outbound not configured for channel/i,
 ];
 
+const STALE_CRON_DELIVERY_MAX_AGE_MS = 3 * 60 * 60_000;
+
 type CompletedDirectCronDelivery = {
   ts: number;
   results: OutboundDeliveryResult[];
@@ -174,6 +176,23 @@ function pruneCompletedDirectCronDeliveries(now: number) {
   }
 }
 
+function resolveCronDeliveryScheduledAtMs(params: { job: CronJob; runStartedAt: number }): number {
+  const scheduledAt = params.job.state?.nextRunAtMs;
+  return typeof scheduledAt === "number" && Number.isFinite(scheduledAt)
+    ? scheduledAt
+    : params.runStartedAt;
+}
+
+function isStaleCronDelivery(params: {
+  job: CronJob;
+  runStartedAt: number;
+  nowMs?: number;
+}): boolean {
+  const nowMs = params.nowMs ?? Date.now();
+  const scheduledAtMs = resolveCronDeliveryScheduledAtMs(params);
+  return nowMs - scheduledAtMs > STALE_CRON_DELIVERY_MAX_AGE_MS;
+}
+
 function rememberCompletedDirectCronDelivery(
   idempotencyKey: string,
   results: readonly OutboundDeliveryResult[],
@@ -331,6 +350,30 @@ export async function dispatchCronDelivery(
           ...params.telemetry,
         });
       }
+      if (
+        params.deliveryRequested &&
+        isStaleCronDelivery({
+          job: params.job,
+          runStartedAt: params.runStartedAt,
+        })
+      ) {
+        deliveryAttempted = true;
+        const scheduledAtMs = resolveCronDeliveryScheduledAtMs({
+          job: params.job,
+          runStartedAt: params.runStartedAt,
+        });
+        logWarn(
+          `[cron:${params.job.id}] skipping stale delivery scheduled at ${new Date(scheduledAtMs).toISOString()}, age ${Math.round((Date.now() - scheduledAtMs) / 60_000)}m`,
+        );
+        return params.withRunSession({
+          status: "ok",
+          summary,
+          outputText,
+          deliveryAttempted,
+          delivered: false,
+          ...params.telemetry,
+        });
+      }
       deliveryAttempted = true;
       const cachedResults = getCompletedDirectCronDelivery(deliveryIdempotencyKey);
       if (cachedResults) {
