fix: address delivery dedupe review follow-ups (#44666)

Merged via squash.

Prepared head SHA: 8e6d254cc4
Co-authored-by: frankekn <4488090+frankekn@users.noreply.github.com>
Co-authored-by: frankekn <4488090+frankekn@users.noreply.github.com>
Reviewed-by: @frankekn

src/agents/subagent-registry.persistence.test.ts

@@ -343,6 +343,35 @@ describe("subagent registry persistence", () => {
     expect(afterSecond.runs["run-3"].cleanupCompletedAt).toBeDefined();
   });
 
+  it("retries cleanup announce after announce flow rejects", async () => {
+    const persisted = createPersistedEndedRun({
+      runId: "run-reject",
+      childSessionKey: "agent:main:subagent:reject",
+      task: "reject announce",
+      cleanup: "keep",
+    });
+    const registryPath = await writePersistedRegistry(persisted);
+
+    announceSpy.mockRejectedValueOnce(new Error("announce boom"));
+    await restartRegistryAndFlush();
+
+    expect(announceSpy).toHaveBeenCalledTimes(1);
+    const afterFirst = JSON.parse(await fs.readFile(registryPath, "utf8")) as {
+      runs: Record<string, { cleanupHandled?: boolean; cleanupCompletedAt?: number }>;
+    };
+    expect(afterFirst.runs["run-reject"].cleanupHandled).toBe(false);
+    expect(afterFirst.runs["run-reject"].cleanupCompletedAt).toBeUndefined();
+
+    announceSpy.mockResolvedValueOnce(true);
+    await restartRegistryAndFlush();
+
+    expect(announceSpy).toHaveBeenCalledTimes(2);
+    const afterSecond = JSON.parse(await fs.readFile(registryPath, "utf8")) as {
+      runs: Record<string, { cleanupCompletedAt?: number }>;
+    };
+    expect(afterSecond.runs["run-reject"].cleanupCompletedAt).toBeDefined();
+  });
+
   it("keeps delete-mode runs retryable when announce is deferred", async () => {
     const persisted = createPersistedEndedRun({
       runId: "run-4",

src/agents/subagent-registry.ts

@@ -534,6 +534,18 @@ function startSubagentAnnounceCleanupFlow(runId: string, entry: SubagentRunRecor
     return false;
   }
   const requesterOrigin = normalizeDeliveryContext(entry.requesterOrigin);
+  const finalizeAnnounceCleanup = (didAnnounce: boolean) => {
+    void finalizeSubagentCleanup(runId, entry.cleanup, didAnnounce).catch((err) => {
+      defaultRuntime.log(`[warn] subagent cleanup finalize failed (${runId}): ${String(err)}`);
+      const current = subagentRuns.get(runId);
+      if (!current || current.cleanupCompletedAt) {
+        return;
+      }
+      current.cleanupHandled = false;
+      persistSubagentRuns();
+    });
+  };
+
   void runSubagentAnnounceFlow({
     childSessionKey: entry.childSessionKey,
     childRunId: entry.runId,
@@ -555,13 +567,13 @@ function startSubagentAnnounceCleanupFlow(runId: string, entry: SubagentRunRecor
     wakeOnDescendantSettle: entry.wakeOnDescendantSettle === true,
   })
     .then((didAnnounce) => {
-      void finalizeSubagentCleanup(runId, entry.cleanup, didAnnounce);
+      finalizeAnnounceCleanup(didAnnounce);
     })
     .catch((error) => {
       defaultRuntime.log(
         `[warn] Subagent announce flow failed during cleanup for run ${runId}: ${String(error)}`,
       );
-      void finalizeSubagentCleanup(runId, entry.cleanup, false);
+      finalizeAnnounceCleanup(false);
     });
   return true;
 }