diff --git a/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts b/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
index 8c0a0b1994d..b4671f3643d 100644
--- a/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
+++ b/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
@@ -585,6 +585,20 @@ describe("isFailoverErrorMessage", () => {
     ]);
   });
 
+  it("matches gateway/websocket connection failures as timeout failover", () => {
+    const samples = [
+      "Connection error.",
+      "gateway not connected",
+      "gateway closed (1006): abnormal closure (no close frame)",
+      "websocket disconnected while waiting for response",
+    ];
+    for (const sample of samples) {
+      expect(isTimeoutErrorMessage(sample)).toBe(true);
+      expect(classifyFailoverReason(sample)).toBe("timeout");
+      expect(isFailoverErrorMessage(sample)).toBe(true);
+    }
+  });
+
   it("matches Gemini MALFORMED_RESPONSE stop reason as timeout (#42149)", () => {
     expectTimeoutFailoverSamples([
       "Unhandled stop reason: MALFORMED_RESPONSE",
diff --git a/src/agents/pi-embedded-helpers/failover-matches.ts b/src/agents/pi-embedded-helpers/failover-matches.ts
index 9f6e83e9461..b521a2ab582 100644
--- a/src/agents/pi-embedded-helpers/failover-matches.ts
+++ b/src/agents/pi-embedded-helpers/failover-matches.ts
@@ -32,6 +32,7 @@ const ERROR_PATTERNS = {
     "deadline exceeded",
     "context deadline exceeded",
     "connection error",
+    "gateway not connected",
     "network error",
     "network request failed",
     "fetch failed",
@@ -47,6 +48,8 @@ const ERROR_PATTERNS = {
     /\benotfound\b/i,
     /\beai_again\b/i,
     /without sending (?:any )?chunks?/i,
+    /\bwebsocket\b.*\b(?:close|closed|disconnect|disconnected|timeout|timed out)\b/i,
+    /\bgateway closed\s*\((?:1006|1012|4000)\b/i,
     /\bstop reason:\s*(?:abort|error|malformed_response|network_error)\b/i,
     /\breason:\s*(?:abort|error|malformed_response|network_error)\b/i,
     /\bunhandled stop reason:\s*(?:abort|error|malformed_response|network_error)\b/i,