diff --git a/packages/ai/CHANGELOG.md b/packages/ai/CHANGELOG.md
index bfa23f06a..ad32ea8c6 100644
--- a/packages/ai/CHANGELOG.md
+++ b/packages/ai/CHANGELOG.md
@@ -11,6 +11,7 @@
 - Fixed Amazon Bedrock prompt-cache points for Claude Fable 5 and Claude Sonnet 5 ([#6235](https://github.com/earendil-works/pi/issues/6235)).
 - Fixed DS4 server context overflow detection for `Prompt has ... tokens, but the configured context size is ... tokens` errors ([#6262](https://github.com/earendil-works/pi/issues/6262)).
 - Fixed OpenAI Codex WebSocket sessions to rotate cached connections before the backend's 60-minute limit, avoiding connection-limit failures on long sessions ([#6268](https://github.com/earendil-works/pi/issues/6268)).
+- Fixed retry classification for Cloudflare 524 timeout responses ([#6239](https://github.com/earendil-works/pi/issues/6239)).
 
 ### Added
 
diff --git a/packages/ai/src/utils/retry.ts b/packages/ai/src/utils/retry.ts
index d3a95a0a4..6f1dd0fd5 100644
--- a/packages/ai/src/utils/retry.ts
+++ b/packages/ai/src/utils/retry.ts
@@ -33,6 +33,7 @@ const RETRYABLE_PROVIDER_ERROR_PATTERN = buildProviderErrorPattern([
 	"502",
 	"503",
 	"504",
+	"524",
 	"service.?unavailable",
 	"server.?error",
 	"internal.?error",
diff --git a/packages/ai/test/retry.test.ts b/packages/ai/test/retry.test.ts
index 17273c70b..9ae6d86f8 100644
--- a/packages/ai/test/retry.test.ts
+++ b/packages/ai/test/retry.test.ts
@@ -33,6 +33,11 @@ describe("provider retry classification", () => {
 		expect(
 			isRetryableAssistantError(fauxAssistantMessage("", { stopReason: "error", errorMessage: "overloaded_error" })),
 		).toBe(true);
+		expect(
+			isRetryableAssistantError(
+				fauxAssistantMessage("", { stopReason: "error", errorMessage: "524 status code (no body)" }),
+			),
+		).toBe(true);
 		expect(isRetryableAssistantError(fauxAssistantMessage("not an error"))).toBe(false);
 	});
 });