fix: reset session after compaction overflow

src/agents/pi-embedded-helpers.test.ts

@@ -7,6 +7,7 @@ import {
   formatAssistantErrorText,
   isBillingErrorMessage,
   isCloudCodeAssistFormatError,
+  isCompactionFailureError,
   isContextOverflowError,
   isFailoverErrorMessage,
   isMessagingToolDuplicate,
@@ -208,6 +209,8 @@ describe("isContextOverflowError", () => {
       "Request exceeds the maximum size",
       "context length exceeded",
       "Maximum context length",
+      "prompt is too long: 208423 tokens > 200000 maximum",
+      "Context overflow: Summarization failed",
       "413 Request Entity Too Large",
     ];
     for (const sample of samples) {
@@ -220,6 +223,26 @@ describe("isContextOverflowError", () => {
   });
 });
 
+describe("isCompactionFailureError", () => {
+  it("matches compaction overflow failures", () => {
+    const samples = [
+      "Context overflow: Summarization failed: 400 {\"message\":\"prompt is too long\"}",
+      "auto-compaction failed due to context overflow",
+      "Compaction failed: prompt is too long",
+    ];
+    for (const sample of samples) {
+      expect(isCompactionFailureError(sample)).toBe(true);
+    }
+  });
+
+  it("ignores non-compaction overflow errors", () => {
+    expect(
+      isCompactionFailureError("Context overflow: prompt too large"),
+    ).toBe(false);
+    expect(isCompactionFailureError("rate limit exceeded")).toBe(false);
+  });
+});
+
 describe("isBillingErrorMessage", () => {
   it("matches credit / payment failures", () => {
     const samples = [

src/agents/pi-embedded-helpers.ts

@@ -244,10 +244,24 @@ export function isContextOverflowError(errorMessage?: string): boolean {
     lower.includes("request exceeds the maximum size") ||
     lower.includes("context length exceeded") ||
     lower.includes("maximum context length") ||
+    lower.includes("prompt is too long") ||
+    lower.includes("context overflow") ||
     (lower.includes("413") && lower.includes("too large"))
   );
 }
 
+export function isCompactionFailureError(errorMessage?: string): boolean {
+  if (!errorMessage) return false;
+  if (!isContextOverflowError(errorMessage)) return false;
+  const lower = errorMessage.toLowerCase();
+  return (
+    lower.includes("summarization failed") ||
+    lower.includes("auto-compaction") ||
+    lower.includes("compaction failed") ||
+    lower.includes("compaction")
+  );
+}
+
 export function formatAssistantErrorText(
   msg: AssistantMessage,
   opts?: { cfg?: ClawdbotConfig; sessionKey?: string },

src/agents/pi-embedded-runner.ts

@@ -36,6 +36,7 @@ import { isCacheEnabled, resolveCacheTtlMs } from "../config/cache-utils.js";
 import type { ClawdbotConfig } from "../config/config.js";
 import { resolveProviderCapabilities } from "../config/provider-capabilities.js";
 import { getMachineDisplayName } from "../infra/machine-name.js";
+import { registerUnhandledRejectionHandler } from "../infra/unhandled-rejections.js";
 import { createSubsystemLogger } from "../logging.js";
 import {
   type enqueueCommand,
@@ -85,6 +86,7 @@ import {
   formatAssistantErrorText,
   isAuthAssistantError,
   isCloudCodeAssistFormatError,
+  isCompactionFailureError,
   isContextOverflowError,
   isFailoverAssistantError,
   isFailoverErrorMessage,
@@ -408,6 +410,13 @@ type EmbeddedPiQueueHandle = {
 const log = createSubsystemLogger("agent/embedded");
 const GOOGLE_TURN_ORDERING_CUSTOM_TYPE = "google-turn-ordering-bootstrap";
 
+registerUnhandledRejectionHandler((reason) => {
+  const message = describeUnknownError(reason);
+  if (!isCompactionFailureError(message)) return false;
+  log.error(`Auto-compaction failed (unhandled): ${message}`);
+  return true;
+});
+
 type CustomEntryLike = { type?: unknown; customType?: unknown };
 
 function hasGoogleTurnOrderingMarker(sessionManager: SessionManager): boolean {