From 4f0a978fc2675460c6ef978df1b5873228b6cb5d Mon Sep 17 00:00:00 2001
From: Ayaan Zaidi <hi@obviy.us>
Date: Tue, 21 Apr 2026 11:05:41 +0530
Subject: [PATCH] fix(cron): track implicit message sends

---
 .../run.message-tool-policy.test.ts           | 47 +++++++++++++++++++
 src/cron/isolated-agent/run.ts                | 31 +++++++++++-
 2 files changed, 77 insertions(+), 1 deletion(-)

diff --git a/src/cron/isolated-agent/run.message-tool-policy.test.ts b/src/cron/isolated-agent/run.message-tool-policy.test.ts
index e4487991e00..ec87cc131f9 100644
--- a/src/cron/isolated-agent/run.message-tool-policy.test.ts
+++ b/src/cron/isolated-agent/run.message-tool-policy.test.ts
@@ -405,6 +405,53 @@ describe("runCronIsolatedAgentTurn message tool policy", () => {
     );
   });
 
+  it("skips cron fallback delivery when the message tool sends to the bound target", async () => {
+    mockRunCronFallbackPassthrough();
+    const params = makeParams();
+    const job = {
+      id: "message-tool-bound-target",
+      name: "Message Tool Bound Target",
+      schedule: { kind: "every", everyMs: 60_000 },
+      sessionTarget: "isolated",
+      payload: { kind: "agentTurn", message: "send a message" },
+      delivery: { mode: "announce", channel: "telegram", to: "123" },
+    } as const;
+    resolveCronDeliveryPlanMock.mockReturnValue({
+      requested: true,
+      mode: "announce",
+      channel: "telegram",
+      to: "123",
+    });
+    runEmbeddedPiAgentMock.mockResolvedValue({
+      payloads: [{ text: "sent" }],
+      didSendViaMessagingTool: true,
+      messagingToolSentTargets: [],
+      meta: { agentMeta: { usage: { input: 10, output: 20 } } },
+    });
+
+    const result = await runCronIsolatedAgentTurn({
+      ...params,
+      job: job as never,
+    });
+
+    expect(dispatchCronDeliveryMock).toHaveBeenCalledTimes(1);
+    expect(dispatchCronDeliveryMock.mock.calls[0]?.[0]).toEqual(
+      expect.objectContaining({
+        deliveryRequested: true,
+        skipMessagingToolDelivery: true,
+      }),
+    );
+    expect(result.delivery).toEqual(
+      expect.objectContaining({
+        intended: { channel: "telegram", to: "123", source: "explicit" },
+        resolved: { ok: true, channel: "telegram", to: "123", source: "explicit" },
+        messageToolSentTo: [{ channel: "telegram", to: "123" }],
+        fallbackUsed: false,
+        delivered: true,
+      }),
+    );
+  });
+
   it("does not mark message tool delivery as matched when cron target resolution failed", async () => {
     mockRunCronFallbackPassthrough();
     resolveCronDeliveryPlanMock.mockReturnValue({
diff --git a/src/cron/isolated-agent/run.ts b/src/cron/isolated-agent/run.ts
index c8b8014451e..9a6e27b199d 100644
--- a/src/cron/isolated-agent/run.ts
+++ b/src/cron/isolated-agent/run.ts
@@ -206,6 +206,32 @@ function buildCronDeliveryTrace(params: {
   };
 }
 
+function resolveMessagingToolSentTargets(params: {
+  resolvedDelivery: ResolvedCronDeliveryTarget;
+  runResult: CronExecutionResult["runResult"];
+}): MessagingToolSend[] {
+  const explicitTargets = params.runResult.messagingToolSentTargets ?? [];
+  if (explicitTargets.length > 0 || params.runResult.didSendViaMessagingTool !== true) {
+    return explicitTargets;
+  }
+  if (!params.resolvedDelivery.ok) {
+    return [];
+  }
+  return [
+    {
+      tool: "message",
+      provider: params.resolvedDelivery.channel,
+      ...(params.resolvedDelivery.accountId
+        ? { accountId: params.resolvedDelivery.accountId }
+        : {}),
+      ...(params.resolvedDelivery.to ? { to: params.resolvedDelivery.to } : {}),
+      ...(params.resolvedDelivery.threadId
+        ? { threadId: String(params.resolvedDelivery.threadId) }
+        : {}),
+    },
+  ];
+}
+
 function resolveCronToolPolicy(params: { deliveryMode: "announce" | "webhook" | "none" }) {
   const enableMessageTool = params.deliveryMode !== "webhook";
   return {
@@ -756,7 +782,10 @@ async function finalizeCronRun(params: {
     matchesMessagingToolDeliveryTarget,
     resolveCronDeliveryBestEffort,
   } = await loadCronDeliveryRuntime();
-  const messagingToolSentTargets = finalRunResult.messagingToolSentTargets ?? [];
+  const messagingToolSentTargets = resolveMessagingToolSentTargets({
+    resolvedDelivery: prepared.resolvedDelivery,
+    runResult: finalRunResult,
+  });
   const didSendViaMessagingTool =
     finalRunResult.didSendViaMessagingTool === true && messagingToolSentTargets.length > 0;
   const skipMessagingToolDelivery =