diff --git a/packages/server/src/server/schedule/service.test.ts b/packages/server/src/server/schedule/service.test.ts
index c71cf6c9a..4dc0f0660 100644
--- a/packages/server/src/server/schedule/service.test.ts
+++ b/packages/server/src/server/schedule/service.test.ts
@@ -171,6 +171,47 @@ describe("ScheduleService", () => {
     );
   });
 
+  test("advances stale nextRunAt on daemon restart", async () => {
+    const service1 = new ScheduleService({
+      paseoHome: tempDir,
+      logger: createTestLogger(),
+      agentManager: new AgentManager({ logger: createTestLogger() }),
+      agentStorage,
+      now: () => now,
+      runner: async () => ({ agentId: null, output: "ok" }),
+    });
+
+    const created = await service1.create({
+      prompt: "Periodic check",
+      cadence: { type: "every", everyMs: 60_000 },
+      target: {
+        type: "new-agent",
+        config: { provider: "claude", cwd: tempDir },
+      },
+    });
+
+    expect(created.nextRunAt).toBe("2026-01-01T00:01:00.000Z");
+    await service1.stop();
+
+    // Simulate daemon restart 10 minutes later
+    now = new Date("2026-01-01T00:10:00.000Z");
+    const service2 = new ScheduleService({
+      paseoHome: tempDir,
+      logger: createTestLogger(),
+      agentManager: new AgentManager({ logger: createTestLogger() }),
+      agentStorage,
+      now: () => now,
+      runner: async () => ({ agentId: null, output: "ok" }),
+    });
+    await service2.start();
+
+    const inspected = await service2.inspect(created.id);
+    expect(
+      new Date(inspected.nextRunAt!).getTime(),
+    ).toBeGreaterThan(now.getTime());
+    await service2.stop();
+  });
+
   test("keeps schedules paused when an in-flight run finishes after pause", async () => {
     let releaseRun: (() => void) | null = null;
     const runStarted = new Promise<void>((resolve) => {
diff --git a/packages/server/src/server/schedule/service.ts b/packages/server/src/server/schedule/service.ts
index 3e874e82b..7fd01cf0e 100644
--- a/packages/server/src/server/schedule/service.ts
+++ b/packages/server/src/server/schedule/service.ts
@@ -251,23 +251,46 @@ export class ScheduleService {
     const schedules = await this.store.list();
     const now = this.now();
     for (const schedule of schedules) {
-      const runningIndex = schedule.runs.findIndex((run) => run.status === "running");
-      if (runningIndex === -1) {
-        continue;
+      let updated = { ...schedule };
+      let dirty = false;
+
+      // Mark any in-flight runs as failed
+      const runningIndex = updated.runs.findIndex(
+        (run) => run.status === "running",
+      );
+      if (runningIndex !== -1) {
+        const runs = [...updated.runs];
+        runs[runningIndex] = {
+          ...runs[runningIndex],
+          status: "failed",
+          endedAt: now.toISOString(),
+          error: "Daemon restarted before the scheduled run completed",
+        };
+        updated = { ...updated, runs };
+        dirty = true;
+      }
+
+      // Advance stale nextRunAt for active schedules
+      if (
+        updated.status === "active" &&
+        updated.nextRunAt &&
+        new Date(updated.nextRunAt).getTime() <= now.getTime()
+      ) {
+        let nextRunAt = computeNextRunAt(
+          updated.cadence,
+          new Date(updated.nextRunAt),
+        );
+        while (nextRunAt.getTime() <= now.getTime()) {
+          nextRunAt = computeNextRunAt(updated.cadence, nextRunAt);
+        }
+        updated = { ...updated, nextRunAt: nextRunAt.toISOString() };
+        dirty = true;
+      }
+
+      if (dirty) {
+        updated = { ...updated, updatedAt: now.toISOString() };
+        await this.store.put(updated);
       }
-      const runs = [...schedule.runs];
-      runs[runningIndex] = {
-        ...runs[runningIndex],
-        status: "failed",
-        endedAt: now.toISOString(),
-        error: "Daemon restarted before the scheduled run completed",
-      };
-      const nextSchedule = {
-        ...schedule,
-        runs,
-        updatedAt: now.toISOString(),
-      };
-      await this.store.put(nextSchedule);
     }
   }