diff --git a/src/auto-reply/reply.triggers.trigger-handling.targets-active-session-native-stop.e2e.test.ts b/src/auto-reply/reply.triggers.trigger-handling.targets-active-session-native-stop.e2e.test.ts
index cec3652d4a9..4ae822c7f35 100644
--- a/src/auto-reply/reply.triggers.trigger-handling.targets-active-session-native-stop.e2e.test.ts
+++ b/src/auto-reply/reply.triggers.trigger-handling.targets-active-session-native-stop.e2e.test.ts
@@ -154,13 +154,31 @@ describe("trigger handling", () => {
         {
           error: "sandbox is not defined.",
           expected:
-            "⚠️ Agent failed before reply: sandbox is not defined.\nLogs: openclaw logs --follow",
+            "Something unexpected happened. Try /new to start a fresh conversation, or try again in a moment.",
         },
         {
           error: "Context window exceeded",
           expected:
             "⚠️ Context overflow — prompt too large for this model. Try a shorter message or a larger-context model.",
         },
+        {
+          error: "rate_limit_exceeded: API rate limit exceeded",
+          expected: "The AI service is busy. Please wait a moment and try again.",
+        },
+        {
+          error: "401 Unauthorized: Invalid API key",
+          expected:
+            "I couldn't connect to the AI service. Please verify your API key is configured correctly.",
+        },
+        {
+          error: "402 Payment Required: billing limit exceeded",
+          expected:
+            "I've reached my limit with the AI service. Please check your account balance and try again.",
+        },
+        {
+          error: "408 Request Timeout: connection timed out",
+          expected: "The request timed out. Please try again, or start a fresh session with /new.",
+        },
       ] as const;
       for (const testCase of errorCases) {
         runEmbeddedPiAgentMock.mockClear();
diff --git a/src/auto-reply/reply/agent-runner-execution.ts b/src/auto-reply/reply/agent-runner-execution.ts
index c25342e4a28..d45e0bb470a 100644
--- a/src/auto-reply/reply/agent-runner-execution.ts
+++ b/src/auto-reply/reply/agent-runner-execution.ts
@@ -7,13 +7,16 @@ import { getCliSessionId } from "../../agents/cli-session.js";
 import { runWithModelFallback } from "../../agents/model-fallback.js";
 import { isCliProvider } from "../../agents/model-selection.js";
 import {
-  BILLING_ERROR_USER_MESSAGE,
+  isAuthErrorMessage,
+  isBillingErrorMessage,
   isCompactionFailureError,
   isContextOverflowError,
-  isBillingErrorMessage,
   isLikelyContextOverflowError,
-  isTransientHttpError,
+  isOverloadedErrorMessage,
+  isRateLimitErrorMessage,
   sanitizeUserFacingText,
+  isTimeoutErrorMessage,
+  isTransientHttpError,
 } from "../../agents/pi-embedded-helpers.js";
 import { runEmbeddedPiAgent } from "../../agents/pi-embedded.js";
 import {
@@ -537,6 +540,12 @@ export async function runAgentTurnWithFallback(params: {
       const isRoleOrderingError = /incorrect role information|roles must alternate/i.test(message);
       const isTransientHttp = isTransientHttpError(message);
 
+      const isRateLimit = isRateLimitErrorMessage(message);
+      const isAuthError = isAuthErrorMessage(message);
+      const isBillingError = isBillingErrorMessage(message);
+      const isTimeoutError = isTimeoutErrorMessage(message);
+      const isOverloaded = isOverloadedErrorMessage(message);
+
       if (
         isCompactionFailure &&
         !didResetAfterCompactionFailure &&
@@ -623,17 +632,30 @@ export async function runAgentTurnWithFallback(params: {
       }
 
       defaultRuntime.error(`Embedded agent failed before reply: ${message}`);
-      const safeMessage = isTransientHttp
-        ? sanitizeUserFacingText(message, { errorContext: true })
-        : message;
-      const trimmedMessage = safeMessage.replace(/\.\s*$/, "");
-      const fallbackText = isBilling
-        ? BILLING_ERROR_USER_MESSAGE
-        : isContextOverflow
-          ? "⚠️ Context overflow — prompt too large for this model. Try a shorter message or a larger-context model."
-          : isRoleOrderingError
-            ? "⚠️ Message ordering conflict - please try again. If this persists, use /new to start a fresh session."
-            : `⚠️ Agent failed before reply: ${trimmedMessage}.\nLogs: openclaw logs --follow`;
+
+      let fallbackText: string;
+
+      if (isContextOverflow) {
+        fallbackText =
+          "⚠️ Context overflow — prompt too large for this model. Try a shorter message or a larger-context model.";
+      } else if (isRoleOrderingError) {
+        fallbackText =
+          "⚠️ Message ordering conflict - please try again. If this persists, use /new to start a fresh session.";
+      } else if (isRateLimit || isOverloaded) {
+        fallbackText = "The AI service is busy. Please wait a moment and try again.";
+      } else if (isAuthError) {
+        fallbackText =
+          "I couldn't connect to the AI service. Please verify your API key is configured correctly.";
+      } else if (isBillingError) {
+        fallbackText =
+          "I've reached my limit with the AI service. Please check your account balance and try again.";
+      } else if (isTimeoutError) {
+        fallbackText =
+          "The request timed out. Please try again, or start a fresh session with /new.";
+      } else {
+        fallbackText =
+          "Something unexpected happened. Try /new to start a fresh conversation, or try again in a moment.";
+      }
 
       return {
         kind: "final",
diff --git a/src/auto-reply/reply/agent-runner.runreplyagent.e2e.test.ts b/src/auto-reply/reply/agent-runner.runreplyagent.e2e.test.ts
index 6bebdc6a390..36fda14def4 100644
--- a/src/auto-reply/reply/agent-runner.runreplyagent.e2e.test.ts
+++ b/src/auto-reply/reply/agent-runner.runreplyagent.e2e.test.ts
@@ -1485,7 +1485,7 @@ describe("runReplyAgent typing (heartbeat)", () => {
       const res = await run();
 
       expect(res).toMatchObject({
-        text: expect.stringContaining("Agent failed before reply"),
+        text: "Something unexpected happened. Try /new to start a fresh conversation, or try again in a moment.",
       });
       expect(sessionStore.main).toBeDefined();
       await expect(fs.access(transcriptPath)).resolves.toBeUndefined();