diff --git a/src/agents/pi-embedded-helpers.iscontextoverflowerror.test.ts b/src/agents/pi-embedded-helpers.iscontextoverflowerror.test.ts
index 19165caa5..79a197326 100644
--- a/src/agents/pi-embedded-helpers.iscontextoverflowerror.test.ts
+++ b/src/agents/pi-embedded-helpers.iscontextoverflowerror.test.ts
@@ -46,4 +46,12 @@ describe("isContextOverflowError", () => {
     expect(isContextOverflowError("model not found")).toBe(false);
     expect(isContextOverflowError("authentication failed")).toBe(false);
   });
+
+  it("ignores normal conversation text mentioning context overflow", () => {
+    // These are legitimate conversation snippets, not error messages
+    expect(isContextOverflowError("Let's investigate the context overflow bug")).toBe(false);
+    expect(isContextOverflowError("The mystery context overflow errors are strange")).toBe(false);
+    expect(isContextOverflowError("We're debugging context overflow issues")).toBe(false);
+    expect(isContextOverflowError("Something is causing context overflow messages")).toBe(false);
+  });
 });
diff --git a/src/agents/pi-embedded-helpers/errors.ts b/src/agents/pi-embedded-helpers/errors.ts
index b47938c23..e368a5c77 100644
--- a/src/agents/pi-embedded-helpers/errors.ts
+++ b/src/agents/pi-embedded-helpers/errors.ts
@@ -20,7 +20,7 @@ export function isContextOverflowError(errorMessage?: string): boolean {
     lower.includes("prompt is too long") ||
     lower.includes("exceeds model context window") ||
     (hasRequestSizeExceeds && hasContextWindow) ||
-    lower.includes("context overflow") ||
+    lower.includes("context overflow:") ||
     (lower.includes("413") && lower.includes("too large"))
   );
 }