diff --git a/packages/server/src/server/schedule/service.test.ts b/packages/server/src/server/schedule/service.test.ts
index 14e0221913..8e37d77e8a 100644
--- a/packages/server/src/server/schedule/service.test.ts
+++ b/packages/server/src/server/schedule/service.test.ts
@@ -1,4 +1,4 @@
-import { mkdir, mkdtemp, rm, writeFile } from "node:fs/promises";
+import { chmod, mkdir, mkdtemp, rm, writeFile } from "node:fs/promises";
 import { join } from "node:path";
 import { tmpdir } from "node:os";
 import { afterEach, beforeEach, describe, expect, test, vi } from "vitest";
@@ -2867,6 +2867,44 @@ describe("ScheduleService", () => {
     expect(inspected.runs[0]?.error).toBe("network blip");
   });
 
+  // chmod cannot make a directory unwritable on Windows or for root.
+  test.skipIf(process.platform === "win32" || process.getuid?.() === 0)(
+    "fires again after a tick whose run could not be recorded",
+    async () => {
+      const service = createScheduleService({
+        paseoHome: tempDir,
+        logger: createTestLogger(),
+        agentManager: new AgentManager({ logger: createTestLogger() }),
+        agentStorage,
+        providerSnapshotManager: NO_UNATTENDED_SCHEDULE_POLICY,
+        now: () => now,
+        runner: async () => ({ agentId: null, output: "ran" }),
+      });
+
+      const created = await service.create({
+        prompt: "ping target",
+        cadence: { type: "every", everyMs: 60_000 },
+        target: { type: "agent", agentId: "88888888-8888-4888-8888-888888888888" },
+      });
+
+      const schedulesDir = join(tempDir, "schedules");
+      now = new Date("2026-01-01T00:01:00.000Z");
+      await chmod(schedulesDir, 0o555);
+      try {
+        await expect(service.tick()).rejects.toThrow();
+      } finally {
+        await chmod(schedulesDir, 0o755);
+      }
+
+      await service.tick();
+
+      const inspected = await service.inspect(created.id);
+      expect(inspected.runs).toHaveLength(1);
+      expect(inspected.runs[0]?.status).toBe("succeeded");
+      expect(inspected.nextRunAt).toBe("2026-01-01T00:02:00.000Z");
+    },
+  );
+
   test("completes the schedule when a scheduled run targets an archived agent", async () => {
     const service = createScheduleService({
       paseoHome: tempDir,
diff --git a/packages/server/src/server/schedule/service.ts b/packages/server/src/server/schedule/service.ts
index 53d2432f88..9dcf27407a 100644
--- a/packages/server/src/server/schedule/service.ts
+++ b/packages/server/src/server/schedule/service.ts
@@ -694,42 +694,44 @@ export class ScheduleService {
   ): Promise<void> {
     const manual = options?.manual === true;
     this.runningScheduleIds.add(schedule.id);
-    const runId = randomUUID();
-    const runningRun: ScheduleRun = {
-      id: runId,
-      scheduledFor: manual ? now.toISOString() : (schedule.nextRunAt ?? now.toISOString()),
-      startedAt: now.toISOString(),
-      endedAt: null,
-      status: "running",
-      agentId: null,
-      output: null,
-      error: null,
-    };
-    const scheduleWithRun = await this.appendRunningRun(schedule.id, runningRun);
-
     try {
-      const result = await this.runner(scheduleWithRun, runId);
-      await this.finishRun({
-        scheduleId: schedule.id,
-        runId,
-        status: "succeeded",
-        agentId: result.agentId,
-        output: result.output,
-        error: null,
-        targetGone: false,
-        manual,
-      });
-    } catch (error) {
-      await this.finishRun({
-        scheduleId: schedule.id,
-        runId,
-        status: "failed",
+      const runId = randomUUID();
+      const runningRun: ScheduleRun = {
+        id: runId,
+        scheduledFor: manual ? now.toISOString() : (schedule.nextRunAt ?? now.toISOString()),
+        startedAt: now.toISOString(),
+        endedAt: null,
+        status: "running",
         agentId: null,
         output: null,
-        error: error instanceof Error ? error.message : String(error),
-        targetGone: error instanceof ScheduleTargetGoneError,
-        manual,
-      });
+        error: null,
+      };
+      const scheduleWithRun = await this.appendRunningRun(schedule.id, runningRun);
+
+      try {
+        const result = await this.runner(scheduleWithRun, runId);
+        await this.finishRun({
+          scheduleId: schedule.id,
+          runId,
+          status: "succeeded",
+          agentId: result.agentId,
+          output: result.output,
+          error: null,
+          targetGone: false,
+          manual,
+        });
+      } catch (error) {
+        await this.finishRun({
+          scheduleId: schedule.id,
+          runId,
+          status: "failed",
+          agentId: null,
+          output: null,
+          error: error instanceof Error ? error.message : String(error),
+          targetGone: error instanceof ScheduleTargetGoneError,
+          manual,
+        });
+      }
     } finally {
       this.runningScheduleIds.delete(schedule.id);
     }