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 ba6f1e6be1f..3a2c08f7939 100644
--- a/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
+++ b/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
@@ -848,6 +848,39 @@ describe("dispatchCronDelivery — double-announce guard", () => {
     );
   });
 
+  it("keeps unresolved message-tool delivery out of delivered status", async () => {
+    const params = makeBaseParams({ synthesizedText: "hello from cron" });
+    params.resolvedDelivery = {
+      ok: false,
+      channel: undefined,
+      to: undefined,
+      accountId: undefined,
+      threadId: undefined,
+      mode: "implicit",
+      error: new Error("sessionKey is required to resolve delivery.channel=last"),
+    };
+    params.unverifiedMessagingToolDelivery = true;
+
+    const state = await dispatchCronDelivery(params);
+
+    expect(deliverOutboundPayloads).not.toHaveBeenCalled();
+    expect(state.delivered).toBe(false);
+    expect(state.deliveryAttempted).toBe(false);
+    expect(state.result).toEqual(
+      expect.objectContaining({
+        status: "error",
+        errorKind: "delivery-target",
+        deliveryAttempted: false,
+      }),
+    );
+    expect(state.result?.error).toContain(
+      "sessionKey is required to resolve delivery.channel=last",
+    );
+    expect(state.result?.error).toContain(
+      "the agent used the message tool, but OpenClaw could not verify",
+    );
+  });
+
   it("builds outbound session context from the run session key under per-channel-peer scoping", async () => {
     vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
     vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
diff --git a/src/cron/isolated-agent/delivery-dispatch.ts b/src/cron/isolated-agent/delivery-dispatch.ts
index b33d91477fa..0bc59d97834 100644
--- a/src/cron/isolated-agent/delivery-dispatch.ts
+++ b/src/cron/isolated-agent/delivery-dispatch.ts
@@ -110,6 +110,7 @@ type DispatchCronDeliveryParams = {
   deliveryRequested: boolean;
   skipHeartbeatDelivery: boolean;
   skipMessagingToolDelivery?: boolean;
+  unverifiedMessagingToolDelivery?: boolean;
   deliveryBestEffort: boolean;
   deliveryPayloadHasStructuredContent: boolean;
   deliveryPayloads: ReplyPayload[];
@@ -445,10 +446,14 @@ export async function dispatchCronDelivery(
   let delivered = skipMessagingToolDelivery;
   let deliveryAttempted = skipMessagingToolDelivery;
   let directCronSessionDeleted = false;
+  const formatDeliveryTargetError = (error: string) =>
+    params.unverifiedMessagingToolDelivery === true
+      ? `${error}; the agent used the message tool, but OpenClaw could not verify that message matched the cron delivery target`
+      : error;
   const failDeliveryTarget = (error: string) =>
     params.withRunSession({
       status: "error",
-      error,
+      error: formatDeliveryTargetError(error),
       errorKind: "delivery-target",
       summary,
       outputText,
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 e0cbdb40959..4f62bc9bd92 100644
--- a/src/cron/isolated-agent/run.message-tool-policy.test.ts
+++ b/src/cron/isolated-agent/run.message-tool-policy.test.ts
@@ -396,6 +396,41 @@ describe("runCronIsolatedAgentTurn message tool policy", () => {
     );
   });
 
+  it("does not mark message tool delivery as matched when cron target resolution failed", async () => {
+    mockRunCronFallbackPassthrough();
+    resolveCronDeliveryPlanMock.mockReturnValue({
+      requested: true,
+      mode: "announce",
+      channel: "last",
+    });
+    resolveDeliveryTargetMock.mockResolvedValue({
+      ok: false,
+      channel: undefined,
+      to: undefined,
+      accountId: undefined,
+      threadId: undefined,
+      mode: "implicit",
+      error: new Error("sessionKey is required to resolve delivery.channel=last"),
+    });
+    runEmbeddedPiAgentMock.mockResolvedValue({
+      payloads: [{ text: "sent" }],
+      didSendViaMessagingTool: true,
+      messagingToolSentTargets: [{ tool: "message", provider: "telegram", to: "123" }],
+      meta: { agentMeta: { usage: { input: 10, output: 20 } } },
+    });
+
+    await runCronIsolatedAgentTurn(makeParams());
+
+    expect(dispatchCronDeliveryMock).toHaveBeenCalledTimes(1);
+    expect(dispatchCronDeliveryMock.mock.calls[0]?.[0]).toEqual(
+      expect.objectContaining({
+        deliveryRequested: true,
+        skipMessagingToolDelivery: false,
+        unverifiedMessagingToolDelivery: true,
+      }),
+    );
+  });
+
   it("marks no-deliver runs delivered when the message tool sends to the current target", async () => {
     mockRunCronFallbackPassthrough();
     resolveCronDeliveryPlanMock.mockReturnValue({
diff --git a/src/cron/isolated-agent/run.test-harness.ts b/src/cron/isolated-agent/run.test-harness.ts
index bfa177a6f0a..31c28312ba9 100644
--- a/src/cron/isolated-agent/run.test-harness.ts
+++ b/src/cron/isolated-agent/run.test-harness.ts
@@ -386,15 +386,22 @@ function resetRunOutcomeMocks(): void {
       deliveryRequested,
       skipHeartbeatDelivery,
       skipMessagingToolDelivery,
+      resolvedDelivery,
     }) => ({
       result: undefined,
       delivered: Boolean(
         skipMessagingToolDelivery ||
-        (deliveryRequested && !skipHeartbeatDelivery && !skipMessagingToolDelivery),
+        (deliveryRequested &&
+          !skipHeartbeatDelivery &&
+          !skipMessagingToolDelivery &&
+          resolvedDelivery.ok),
       ),
       deliveryAttempted: Boolean(
         skipMessagingToolDelivery ||
-        (deliveryRequested && !skipHeartbeatDelivery && !skipMessagingToolDelivery),
+        (deliveryRequested &&
+          !skipHeartbeatDelivery &&
+          !skipMessagingToolDelivery &&
+          resolvedDelivery.ok),
       ),
       summary,
       outputText,
diff --git a/src/cron/isolated-agent/run.ts b/src/cron/isolated-agent/run.ts
index 5288a510b64..ca1d6aaba5f 100644
--- a/src/cron/isolated-agent/run.ts
+++ b/src/cron/isolated-agent/run.ts
@@ -662,17 +662,19 @@ async function finalizeCronRun(params: {
     matchesMessagingToolDeliveryTarget,
     resolveCronDeliveryBestEffort,
   } = await loadCronDeliveryRuntime();
+  const messagingToolSentTargets = finalRunResult.messagingToolSentTargets ?? [];
+  const didSendViaMessagingTool =
+    finalRunResult.didSendViaMessagingTool === true && messagingToolSentTargets.length > 0;
   const skipMessagingToolDelivery =
-    finalRunResult.didSendViaMessagingTool === true &&
-    (prepared.resolvedDelivery.ok
-      ? (finalRunResult.messagingToolSentTargets ?? []).some((target) =>
-          matchesMessagingToolDeliveryTarget(target, {
-            channel: prepared.resolvedDelivery.channel,
-            to: prepared.resolvedDelivery.to,
-            accountId: prepared.resolvedDelivery.accountId,
-          }),
-        )
-      : (finalRunResult.messagingToolSentTargets ?? []).length > 0);
+    didSendViaMessagingTool &&
+    prepared.resolvedDelivery.ok &&
+    messagingToolSentTargets.some((target) =>
+      matchesMessagingToolDeliveryTarget(target, {
+        channel: prepared.resolvedDelivery.channel,
+        to: prepared.resolvedDelivery.to,
+        accountId: prepared.resolvedDelivery.accountId,
+      }),
+    );
   const deliveryResult = await dispatchCronDelivery({
     cfg: prepared.input.cfg,
     cfgWithAgentDefaults: prepared.cfgWithAgentDefaults,
@@ -687,6 +689,7 @@ async function finalizeCronRun(params: {
     deliveryRequested: prepared.deliveryRequested,
     skipHeartbeatDelivery,
     skipMessagingToolDelivery,
+    unverifiedMessagingToolDelivery: didSendViaMessagingTool && !prepared.resolvedDelivery.ok,
     deliveryBestEffort: resolveCronDeliveryBestEffort(prepared.input.job),
     deliveryPayloadHasStructuredContent,
     deliveryPayloads,