diff --git a/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts b/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
index 7dfe826e158..a78cf977729 100644
--- a/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
+++ b/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
@@ -648,6 +648,12 @@ describe("classifyFailoverReason", () => {
     expect(classifyFailoverReason("410 conversation expired")).toBe("session_expired");
   });
 
+  it("classifies 'No conversation found' from Claude CLI as session_expired", () => {
+    expect(classifyFailoverReason("No conversation found with session ID: abc123")).toBe(
+      "session_expired",
+    );
+  });
+
   it("keeps explicit billing and auth signals on 410 text", () => {
     expect(classifyFailoverReason("HTTP 410: invalid_api_key")).toBe("auth");
     expect(classifyFailoverReason("HTTP 410: authentication failed")).toBe("auth");
diff --git a/src/agents/pi-embedded-helpers/errors.ts b/src/agents/pi-embedded-helpers/errors.ts
index e81407f6e9c..68deb227ae0 100644
--- a/src/agents/pi-embedded-helpers/errors.ts
+++ b/src/agents/pi-embedded-helpers/errors.ts
@@ -1109,6 +1109,7 @@ function isCliSessionExpiredErrorMessage(raw: string): boolean {
     lower.includes("session expired") ||
     lower.includes("session invalid") ||
     lower.includes("conversation not found") ||
+    lower.includes("no conversation found") ||
     lower.includes("conversation does not exist") ||
     lower.includes("conversation expired") ||
     lower.includes("conversation invalid") ||