diff --git a/CHANGELOG.md b/CHANGELOG.md
index 05b54daf3e7..80c96538260 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,16 +4,11 @@ Docs: https://docs.openclaw.ai
 
 ## Unreleased
 
-### Fixes
-
-- Cron/failover: classify structured OpenAI-compatible `server_error` payloads as `server_error`, expose that reason in cron state, and let one-shot cron retry policy honor `retryOn: ["server_error"]` without requiring raw `5xx` text. (#45594) Thanks @clovericbot.
-
-## 2026.5.8
-
 ### Changes
 
 ### Fixes
 
+- Cron/failover: classify structured OpenAI-compatible `server_error` payloads as `server_error`, expose that reason in cron state, and let one-shot cron retry policy honor `retryOn: ["server_error"]` without requiring raw `5xx` text. (#45594) Thanks @clovericbot.
 - Feishu: auto-thread `message(action="send")` replies inside the topic when the active session is group_topic or group_topic_sender, and propagate `replyInThread` through text, card, and media outbound adapters so topic-scoped sessions no longer post at the group root. Fixes #74903. (#77151) Thanks @ai-hpc.
 - WhatsApp: pass routing context into voice-note transcript echo preflight so echoed transcripts can deliver to the originating chat. Fixes #79778. (#79788) Thanks @hclsys.
 
diff --git a/src/agents/failover-error.test.ts b/src/agents/failover-error.test.ts
index 133e20952de..c853b329e06 100644
--- a/src/agents/failover-error.test.ts
+++ b/src/agents/failover-error.test.ts
@@ -986,9 +986,16 @@ describe("failover-error", () => {
         message: OPENAI_SERVER_ERROR_PAYLOAD,
       }),
     ).toBe("server_error");
+    expect(
+      resolveFailoverReasonFromError({
+        status: 500,
+        message: OPENAI_SERVER_ERROR_PAYLOAD,
+      }),
+    ).toBe("server_error");
 
     const err = coerceToFailoverError(
       {
+        status: 500,
         message: OPENAI_SERVER_ERROR_PAYLOAD,
       },
       { provider: "openai-codex", model: "gpt-5.4" },
diff --git a/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts b/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
index 6bcc719c6ad..ae8f5f6ad83 100644
--- a/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
+++ b/src/agents/pi-embedded-helpers.isbillingerrormessage.test.ts
@@ -683,6 +683,19 @@ describe("classifyFailoverReasonFromHttpStatus", () => {
     expect(classifyFailoverReasonFromHttpStatus(422, payload)).toBe("format");
   });
 
+  it("preserves structured server_error markers on explicit HTTP 5xx statuses", () => {
+    expect(classifyFailoverReasonFromHttpStatus(500, OPENAI_SERVER_ERROR_PAYLOAD)).toBe(
+      "server_error",
+    );
+    expect(classifyFailoverReasonFromHttpStatus(502, OPENAI_SERVER_ERROR_PAYLOAD)).toBe(
+      "server_error",
+    );
+    expect(classifyFailoverReasonFromHttpStatus(504, OPENAI_SERVER_ERROR_PAYLOAD)).toBe(
+      "server_error",
+    );
+    expect(classifyFailoverReasonFromHttpStatus(500)).toBe("timeout");
+  });
+
   it("treats generic HTTP 410 responses as retryable timeouts", () => {
     expect(classifyFailoverReasonFromHttpStatus(410)).toBe("timeout");
     expect(classifyFailoverReasonFromHttpStatus(410, "")).toBe("timeout");
diff --git a/src/agents/pi-embedded-helpers/errors.ts b/src/agents/pi-embedded-helpers/errors.ts
index 393e811186b..2a5de90000e 100644
--- a/src/agents/pi-embedded-helpers/errors.ts
+++ b/src/agents/pi-embedded-helpers/errors.ts
@@ -697,6 +697,9 @@ function classifyFailoverClassificationFromHttpStatus(
     return toReasonClassification("timeout");
   }
   if (status === 500 || status === 502 || status === 504) {
+    if (messageReason === "server_error") {
+      return messageClassification;
+    }
     return toReasonClassification("timeout");
   }
   if (status === 529) {