diff --git a/src/cron/service.update-recompute-drops-due-every.test.ts b/src/cron/service.update-recompute-drops-due-every.test.ts
index 18e3776f5eb6..4c5b7db20ad1 100644
--- a/src/cron/service.update-recompute-drops-due-every.test.ts
+++ b/src/cron/service.update-recompute-drops-due-every.test.ts
@@ -73,51 +73,91 @@ describe("update() must not drop a due every-job's pending run", () => {
     cron.stop();
   });
 
-  it("re-anchors an every-job to the edit time when the interval actually changes", async () => {
-    const store = await makeStorePath();
-    const base = Date.parse("2025-12-13T00:00:00.000Z");
+  it.each([
+    { name: "before its first run", previousEveryMs: 10_000, nextEveryMs: 3_600_000 },
+    {
+      name: "after a completed run when the interval increases",
+      previousEveryMs: 10_000,
+      nextEveryMs: 3_600_000,
+      completedRun: true,
+    },
+    {
+      name: "after a completed run when the interval decreases",
+      previousEveryMs: 60_000,
+      nextEveryMs: 10_000,
+      completedRun: true,
+    },
+    {
+      name: "at an explicit future anchor after a completed run",
+      previousEveryMs: 10_000,
+      nextEveryMs: 3_600_000,
+      completedRun: true,
+      futureAnchorOffsetMs: 7_200_000,
+    },
+  ])(
+    "re-anchors an every-job $name",
+    async ({ previousEveryMs, nextEveryMs, completedRun, futureAnchorOffsetMs }) => {
+      const store = await makeStorePath();
+      const base = Date.parse("2025-12-13T00:00:00.000Z");
 
-    const finished = createFinishedBarrier();
-    const cron = new CronService({
-      storePath: store.storePath,
-      cronEnabled: true,
-      log: noopLogger,
-      enqueueSystemEvent: vi.fn(),
-      requestHeartbeat: vi.fn(),
-      runIsolatedAgentJob: vi.fn(async () => ({ status: "ok" as const })),
-      onEvent: finished.onEvent,
-    });
+      const finished = createFinishedBarrier();
+      const cron = new CronService({
+        storePath: store.storePath,
+        cronEnabled: true,
+        log: noopLogger,
+        enqueueSystemEvent: vi.fn(),
+        requestHeartbeat: vi.fn(),
+        runIsolatedAgentJob: vi.fn(async () => ({ status: "ok" as const })),
+        onEvent: finished.onEvent,
+      });
 
-    await cron.start();
+      await cron.start();
 
-    const job = await cron.add({
-      name: "every 10s",
-      enabled: true,
-      schedule: { kind: "every", everyMs: 10_000 },
-      sessionTarget: "isolated",
-      wakeMode: "next-heartbeat",
-      payload: { kind: "agentTurn", message: "tick" },
-    });
-    const jobId = job.id;
-    expect(job.schedule).toMatchObject({ kind: "every", anchorMs: base });
+      const job = await cron.add({
+        name: "every 10s",
+        enabled: true,
+        schedule: { kind: "every", everyMs: previousEveryMs },
+        sessionTarget: "isolated",
+        wakeMode: "next-heartbeat",
+        payload: { kind: "agentTurn", message: "tick" },
+      });
+      const jobId = job.id;
+      expect(job.schedule).toMatchObject({ kind: "every", anchorMs: base });
 
-    // User edits the interval from 10s to 1h. The control UI omits the internal
-    // anchorMs, so the new cadence must start from the edit time rather than
-    // keeping the old phase; nextRunAtMs is one new interval from now.
-    const editTime = base + 3_000;
-    vi.setSystemTime(new Date(editTime));
-    await cron.update(jobId, { schedule: { kind: "every", everyMs: 3_600_000 } });
+      let editTime = base + 3_000;
+      if (completedRun) {
+        vi.setSystemTime(new Date(base + previousEveryMs + 5));
+        const firstRun = finished.waitForOk(jobId);
+        await vi.runOnlyPendingTimersAsync();
+        await firstRun;
+        const completedJob = (await cron.list({ includeDisabled: true })).find(
+          (candidate) => candidate.id === jobId,
+        )!;
+        editTime = completedJob.state.lastRunAtMs! + 3_000;
+      }
 
-    const current = (await cron.list({ includeDisabled: true })).find((j) => j.id === jobId)!;
-    expect(current.schedule).toMatchObject({
-      kind: "every",
-      everyMs: 3_600_000,
-      anchorMs: editTime,
-    });
-    expect(current.state.nextRunAtMs).toBe(editTime + 3_600_000);
+      vi.setSystemTime(new Date(editTime));
+      const futureAnchorMs =
+        futureAnchorOffsetMs === undefined ? undefined : editTime + futureAnchorOffsetMs;
+      await cron.update(jobId, {
+        schedule: {
+          kind: "every",
+          everyMs: nextEveryMs,
+          ...(futureAnchorMs === undefined ? {} : { anchorMs: futureAnchorMs }),
+        },
+      });
 
-    cron.stop();
-  });
+      const current = (await cron.list({ includeDisabled: true })).find((j) => j.id === jobId)!;
+      expect(current.schedule).toMatchObject({
+        kind: "every",
+        everyMs: nextEveryMs,
+        anchorMs: futureAnchorMs ?? editTime,
+      });
+      expect(current.state.nextRunAtMs).toBe(futureAnchorMs ?? editTime + nextEveryMs);
+
+      cron.stop();
+    },
+  );
 
   it("preserves a due cron-job nextRunAtMs on an idempotent schedule re-save", async () => {
     const store = await makeStorePath();
diff --git a/src/cron/service/jobs-scheduling.ts b/src/cron/service/jobs-scheduling.ts
index e063b485a793..e57f76842b12 100644
--- a/src/cron/service/jobs-scheduling.ts
+++ b/src/cron/service/jobs-scheduling.ts
@@ -323,8 +323,13 @@ export function computeJobNextRunAtMs(job: CronJob, nowMs: number): number | und
     if (everyMs < 1) {
       return undefined;
     }
+    const fallbackAnchorMs = isFiniteTimestamp(job.createdAtMs) ? job.createdAtMs : nowMs;
+    const anchorMs = resolveEveryAnchorMs({
+      schedule: job.schedule,
+      fallbackAnchorMs,
+    });
     const lastRunAtMs = job.state.lastRunAtMs;
-    if (isFiniteTimestamp(lastRunAtMs)) {
+    if (isFiniteTimestamp(lastRunAtMs) && lastRunAtMs >= anchorMs) {
       const nextFromLastRun = Math.floor(lastRunAtMs) + everyMs;
       if (!isFiniteTimestamp(nextFromLastRun)) {
         return undefined;
@@ -333,11 +338,6 @@ export function computeJobNextRunAtMs(job: CronJob, nowMs: number): number | und
         return nextFromLastRun;
       }
     }
-    const fallbackAnchorMs = isFiniteTimestamp(job.createdAtMs) ? job.createdAtMs : nowMs;
-    const anchorMs = resolveEveryAnchorMs({
-      schedule: job.schedule,
-      fallbackAnchorMs,
-    });
     const next = computeNextRunAtMs({ ...job.schedule, everyMs, anchorMs }, nowMs);
     return isFiniteTimestamp(next) ? next : undefined;
   }