From 700a8e8dd0cc81059f47b8e13d25dc0bdaf8d99d Mon Sep 17 00:00:00 2001
From: Ted Li <tl2493@columbia.edu>
Date: Thu, 16 Apr 2026 13:23:02 -0700
Subject: [PATCH] Cron: clean up deleteAfterRun direct deliveries

---
 .../delivery-dispatch.double-announce.test.ts | 56 +++++++++++++++++++
 src/cron/isolated-agent/delivery-dispatch.ts  | 23 +++++---
 2 files changed, 72 insertions(+), 7 deletions(-)

diff --git a/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts b/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
index 52dc888b592..ec3f37dc76d 100644
--- a/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
+++ b/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
@@ -852,6 +852,34 @@ describe("dispatchCronDelivery — double-announce guard", () => {
     );
   });
 
+  it("cleans up the direct cron session after threaded direct delivery when deleteAfterRun is enabled", async () => {
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({ synthesizedText: "Final weather summary" });
+    params.resolvedDelivery = {
+      ...makeResolvedDelivery(),
+      mode: "implicit",
+      threadId: 42,
+    };
+    (params.job as { deleteAfterRun?: boolean }).deleteAfterRun = true;
+
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.result).toBeUndefined();
+    expect(state.delivered).toBe(true);
+    expect(deliverOutboundPayloads).toHaveBeenCalledTimes(1);
+    expect(callGateway).toHaveBeenCalledWith({
+      method: "sessions.delete",
+      params: {
+        key: "agent:main",
+        deleteTranscript: true,
+        emitLifecycleHooks: false,
+      },
+      timeoutMs: 10_000,
+    });
+  });
+
   it("delivers structured heartbeat/media payloads once through the outbound adapter", async () => {
     vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
     vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
@@ -883,6 +911,33 @@ describe("dispatchCronDelivery — double-announce guard", () => {
     );
   });
 
+  it("cleans up the direct cron session after structured direct delivery when deleteAfterRun is enabled", async () => {
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({ synthesizedText: "HEARTBEAT_OK" });
+    params.deliveryPayloadHasStructuredContent = true;
+    params.deliveryPayloads = [
+      { text: "HEARTBEAT_OK", mediaUrl: "https://example.com/img.png" },
+    ] as never;
+    (params.job as { deleteAfterRun?: boolean }).deleteAfterRun = true;
+
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.result).toBeUndefined();
+    expect(state.delivered).toBe(true);
+    expect(deliverOutboundPayloads).toHaveBeenCalledTimes(1);
+    expect(callGateway).toHaveBeenCalledWith({
+      method: "sessions.delete",
+      params: {
+        key: "agent:main",
+        deleteTranscript: true,
+        emitLifecycleHooks: false,
+      },
+      timeoutMs: 10_000,
+    });
+  });
+
   it("suppresses NO_REPLY payload with surrounding whitespace", async () => {
     vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
     vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
@@ -965,6 +1020,7 @@ describe("dispatchCronDelivery — double-announce guard", () => {
       },
       timeoutMs: 10_000,
     });
+    expect(callGateway).toHaveBeenCalledTimes(1);
   });
 
   it("suppresses trailing NO_REPLY after summary text in direct delivery (#64976)", async () => {
diff --git a/src/cron/isolated-agent/delivery-dispatch.ts b/src/cron/isolated-agent/delivery-dispatch.ts
index 687bebfbac8..085ada30644 100644
--- a/src/cron/isolated-agent/delivery-dispatch.ts
+++ b/src/cron/isolated-agent/delivery-dispatch.ts
@@ -441,6 +441,7 @@ export async function dispatchCronDelivery(
   // remains the only source of delivered state.
   let delivered = skipMessagingToolDelivery;
   let deliveryAttempted = skipMessagingToolDelivery;
+  let directCronSessionDeleted = false;
   const failDeliveryTarget = (error: string) =>
     params.withRunSession({
       status: "error",
@@ -452,7 +453,7 @@ export async function dispatchCronDelivery(
       ...params.telemetry,
     });
   const cleanupDirectCronSessionIfNeeded = async (): Promise<void> => {
-    if (!params.job.deleteAfterRun) {
+    if (!params.job.deleteAfterRun || directCronSessionDeleted) {
       return;
     }
     try {
@@ -466,6 +467,7 @@ export async function dispatchCronDelivery(
         },
         timeoutMs: 10_000,
       });
+      directCronSessionDeleted = true;
     } catch {
       // Best-effort; direct delivery result should still be returned.
     }
@@ -648,6 +650,17 @@ export async function dispatchCronDelivery(
     }
   };
 
+  const deliverViaDirectAndCleanup = async (
+    delivery: SuccessfulDeliveryTarget,
+    options?: { retryTransient?: boolean },
+  ): Promise<RunCronAgentTurnResult | null> => {
+    try {
+      return await deliverViaDirect(delivery, options);
+    } finally {
+      await cleanupDirectCronSessionIfNeeded();
+    }
+  };
+
   const finalizeTextDelivery = async (
     delivery: SuccessfulDeliveryTarget,
   ): Promise<RunCronAgentTurnResult | null> => {
@@ -758,11 +771,7 @@ export async function dispatchCronDelivery(
         ...params.telemetry,
       });
     }
-    try {
-      return await deliverViaDirect(delivery, { retryTransient: true });
-    } finally {
-      await cleanupDirectCronSessionIfNeeded();
-    }
+    return await deliverViaDirectAndCleanup(delivery, { retryTransient: true });
   };
 
   if (params.deliveryRequested && !params.skipHeartbeatDelivery && !skipMessagingToolDelivery) {
@@ -802,7 +811,7 @@ export async function dispatchCronDelivery(
     const useDirectDelivery =
       params.deliveryPayloadHasStructuredContent || params.resolvedDelivery.threadId != null;
     if (useDirectDelivery) {
-      const directResult = await deliverViaDirect(params.resolvedDelivery);
+      const directResult = await deliverViaDirectAndCleanup(params.resolvedDelivery);
       if (directResult) {
         return {
           result: directResult,