diff --git a/src/cron/isolated-agent.uses-last-non-empty-agent-text-as.test.ts b/src/cron/isolated-agent.uses-last-non-empty-agent-text-as.test.ts
index 353d92e1b85..3a4e9d91cd2 100644
--- a/src/cron/isolated-agent.uses-last-non-empty-agent-text-as.test.ts
+++ b/src/cron/isolated-agent.uses-last-non-empty-agent-text-as.test.ts
@@ -197,6 +197,50 @@ describe("runCronIsolatedAgentTurn", () => {
     });
   });
 
+  it("treats transient error payloads as non-fatal when a later success payload exists", async () => {
+    await withTempHome(async (home) => {
+      mockEmbeddedPayloads([
+        {
+          text: "⚠️ ✍️ Write: failed",
+          isError: true,
+        },
+        {
+          text: "Write completed successfully.",
+          isError: false,
+        },
+      ]);
+      const { res } = await runCronTurn(home, {
+        jobPayload: DEFAULT_AGENT_TURN_PAYLOAD,
+        mockTexts: null,
+      });
+
+      expect(res.status).toBe("ok");
+      expect(res.summary).toBe("Write completed successfully.");
+    });
+  });
+
+  it("keeps error status when run-level error accompanies post-error text", async () => {
+    await withTempHome(async (home) => {
+      vi.mocked(runEmbeddedPiAgent).mockResolvedValue({
+        payloads: [
+          { text: "Model context overflow", isError: true },
+          { text: "Partial assistant text before error" },
+        ],
+        meta: {
+          durationMs: 5,
+          agentMeta: { sessionId: "s", provider: "p", model: "m" },
+          error: { kind: "context_overflow", message: "exceeded context window" },
+        },
+      });
+      const { res } = await runCronTurn(home, {
+        jobPayload: DEFAULT_AGENT_TURN_PAYLOAD,
+        mockTexts: null,
+      });
+
+      expect(res.status).toBe("error");
+    });
+  });
+
   it("passes resolved agentDir to runEmbeddedPiAgent", async () => {
     await withTempHome(async (home) => {
       const { res } = await runCronTurn(home, {
diff --git a/src/cron/isolated-agent/run.ts b/src/cron/isolated-agent/run.ts
index d4f1f1d6d59..445001b93f4 100644
--- a/src/cron/isolated-agent/run.ts
+++ b/src/cron/isolated-agent/run.ts
@@ -570,17 +570,29 @@ export async function runCronIsolatedAgentTurn(params: {
     Object.keys(deliveryPayload?.channelData ?? {}).length > 0;
   const deliveryBestEffort = resolveCronDeliveryBestEffort(params.job);
   const hasErrorPayload = payloads.some((payload) => payload?.isError === true);
+  const runLevelError = runResult.meta?.error;
+  const lastErrorPayloadIndex = payloads.findLastIndex((payload) => payload?.isError === true);
+  const hasSuccessfulPayloadAfterLastError =
+    !runLevelError &&
+    lastErrorPayloadIndex >= 0 &&
+    payloads
+      .slice(lastErrorPayloadIndex + 1)
+      .some((payload) => payload?.isError !== true && Boolean(payload?.text?.trim()));
+  // Tool wrappers can emit transient/false-positive error payloads before a valid final
+  // assistant payload.  Only treat payload errors as recoverable when (a) the run itself
+  // did not report a model/context-level error and (b) a non-error payload follows.
+  const hasFatalErrorPayload = hasErrorPayload && !hasSuccessfulPayloadAfterLastError;
   const lastErrorPayloadText = [...payloads]
     .toReversed()
     .find((payload) => payload?.isError === true && Boolean(payload?.text?.trim()))
     ?.text?.trim();
-  const embeddedRunError = hasErrorPayload
+  const embeddedRunError = hasFatalErrorPayload
     ? (lastErrorPayloadText ?? "cron isolated run returned an error payload")
     : undefined;
   const resolveRunOutcome = (params?: { delivered?: boolean; deliveryAttempted?: boolean }) =>
     withRunSession({
-      status: hasErrorPayload ? "error" : "ok",
-      ...(hasErrorPayload
+      status: hasFatalErrorPayload ? "error" : "ok",
+      ...(hasFatalErrorPayload
         ? { error: embeddedRunError ?? "cron isolated run returned an error payload" }
         : {}),
       summary,
@@ -637,7 +649,7 @@ export async function runCronIsolatedAgentTurn(params: {
       deliveryAttempted:
         deliveryResult.result.deliveryAttempted ?? deliveryResult.deliveryAttempted,
     };
-    if (!hasErrorPayload || deliveryResult.result.status !== "ok") {
+    if (!hasFatalErrorPayload || deliveryResult.result.status !== "ok") {
       return resultWithDeliveryMeta;
     }
     return resolveRunOutcome({