fix(cron): treat announce delivery failure as ok when execution succeeded (#31082)

* cron: treat announce delivery failure as ok when agent execution succeeded

* fix: set delivered:false and error on announce delivery failure paths

* Changelog: note cron announce delivery status handling (#31082)

---------

Co-authored-by: Tak Hoffman <781889+Takhoffman@users.noreply.github.com>

src/cron/isolated-agent.skips-delivery-without-whatsapp-recipient-besteffortdeliver-true.test.ts

@@ -317,11 +317,33 @@ describe("runCronIsolatedAgentTurn", () => {
     });
   });
 
-  it("fails when announce delivery reports false and best-effort is disabled", async () => {
-    const { res, deps } = await runAnnounceFlowResult(false);
-    expect(res.status).toBe("error");
-    expect(res.error).toContain("cron announce delivery failed");
-    expect(deps.sendMessageTelegram).not.toHaveBeenCalled();
+  it("returns ok when announce delivery reports false and best-effort is disabled", async () => {
+    await withTempCronHome(async (home) => {
+      const storePath = await writeSessionStore(home, { lastProvider: "webchat", lastTo: "" });
+      const deps = createCliDeps();
+      mockAgentPayloads([{ text: "hello from cron" }]);
+      vi.mocked(runSubagentAnnounceFlow).mockResolvedValueOnce(false);
+
+      const res = await runTelegramAnnounceTurn({
+        home,
+        storePath,
+        deps,
+        delivery: {
+          mode: "announce",
+          channel: "telegram",
+          to: "123",
+          bestEffort: false,
+        },
+      });
+
+      // Announce delivery failure should not mark a successful agent execution
+      // as error. The execution succeeded; only delivery failed.
+      expect(res.status).toBe("ok");
+      expect(res.delivered).toBe(false);
+      expect(res.deliveryAttempted).toBe(true);
+      expect(res.error).toBe("cron announce delivery failed");
+      expect(deps.sendMessageTelegram).not.toHaveBeenCalled();
+    });
   });
 
   it("marks attempted when announce delivery reports false and best-effort is enabled", async () => {
@@ -333,6 +355,37 @@ describe("runCronIsolatedAgentTurn", () => {
     expect(deps.sendMessageTelegram).not.toHaveBeenCalled();
   });
 
+  it("returns ok when announce flow throws and best-effort is disabled", async () => {
+    await withTempCronHome(async (home) => {
+      const storePath = await writeSessionStore(home, { lastProvider: "webchat", lastTo: "" });
+      const deps = createCliDeps();
+      mockAgentPayloads([{ text: "hello from cron" }]);
+      vi.mocked(runSubagentAnnounceFlow).mockRejectedValueOnce(
+        new Error("gateway closed (1008): pairing required"),
+      );
+
+      const res = await runTelegramAnnounceTurn({
+        home,
+        storePath,
+        deps,
+        delivery: {
+          mode: "announce",
+          channel: "telegram",
+          to: "123",
+          bestEffort: false,
+        },
+      });
+
+      // Even when announce throws (e.g. "pairing required"), the agent
+      // execution succeeded so the job status should be ok.
+      expect(res.status).toBe("ok");
+      expect(res.delivered).toBe(false);
+      expect(res.deliveryAttempted).toBe(true);
+      expect(res.error).toContain("pairing required");
+      expect(deps.sendMessageTelegram).not.toHaveBeenCalled();
+    });
+  });
+
   it("ignores structured direct delivery failures when best-effort is enabled", async () => {
     await expectBestEffortTelegramNotDelivered({
       text: "hello from cron",

src/cron/isolated-agent/delivery-dispatch.ts

@@ -326,31 +326,39 @@ export async function dispatchCronDelivery(
       if (didAnnounce) {
         delivered = true;
       } else {
+        // Announce delivery failed but the agent execution itself succeeded.
+        // Return ok so the job isn't penalized for a transient delivery issue
+        // (e.g. "pairing required" when no active client session exists).
+        // Delivery failure is tracked separately via delivered/deliveryAttempted.
         const message = "cron announce delivery failed";
+        logWarn(`[cron:${params.job.id}] ${message}`);
         if (!params.deliveryBestEffort) {
           return params.withRunSession({
-            status: "error",
+            status: "ok",
             summary,
             outputText,
             error: message,
+            delivered: false,
             deliveryAttempted,
             ...params.telemetry,
           });
         }
-        logWarn(`[cron:${params.job.id}] ${message}`);
       }
     } catch (err) {
+      // Same as above: announce delivery errors should not mark a successful
+      // agent execution as failed.
+      logWarn(`[cron:${params.job.id}] ${String(err)}`);
       if (!params.deliveryBestEffort) {
         return params.withRunSession({
-          status: "error",
+          status: "ok",
           summary,
           outputText,
           error: String(err),
+          delivered: false,
           deliveryAttempted,
           ...params.telemetry,
         });
       }
-      logWarn(`[cron:${params.job.id}] ${String(err)}`);
     }
     return null;
   };