diff --git a/CHANGELOG.md b/CHANGELOG.md
index 40306679b..73355315d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@ Docs: https://docs.clawd.bot
 - BlueBubbles: stop typing indicator on idle/no-reply. (#1439) Thanks @Nicell.
 - Auto-reply: only report a model switch when session state is available. (#1465) Thanks @robbyczgw-cla.
 - Control UI: resolve local avatar URLs with basePath across injection + identity RPC. (#1457) Thanks @dlauer.
+- Agents: surface concrete API error details instead of generic AI service errors.
 
 ## 2026.1.21-2
 
diff --git a/src/agents/pi-embedded-helpers.formatassistanterrortext.test.ts b/src/agents/pi-embedded-helpers.formatassistanterrortext.test.ts
index e0a4c897c..e8c514a32 100644
--- a/src/agents/pi-embedded-helpers.formatassistanterrortext.test.ts
+++ b/src/agents/pi-embedded-helpers.formatassistanterrortext.test.ts
@@ -43,8 +43,6 @@ describe("formatAssistantErrorText", () => {
     const msg = makeAssistantError(
       '{"type":"error","error":{"message":"Something exploded","type":"server_error"}}',
     );
-    expect(formatAssistantErrorText(msg)).toBe(
-      "The AI service returned an error. Please try again.",
-    );
+    expect(formatAssistantErrorText(msg)).toBe("LLM error server_error: Something exploded");
   });
 });
diff --git a/src/agents/pi-embedded-helpers.formatrawassistanterrorforui.test.ts b/src/agents/pi-embedded-helpers.formatrawassistanterrorforui.test.ts
index 09e5e443a..9dbadf777 100644
--- a/src/agents/pi-embedded-helpers.formatrawassistanterrorforui.test.ts
+++ b/src/agents/pi-embedded-helpers.formatrawassistanterrorforui.test.ts
@@ -17,4 +17,10 @@ describe("formatRawAssistantErrorForUi", () => {
   it("renders a generic unknown error message when raw is empty", () => {
     expect(formatRawAssistantErrorForUi("")).toContain("unknown error");
   });
+
+  it("formats plain HTTP status lines", () => {
+    expect(formatRawAssistantErrorForUi("500 Internal Server Error")).toBe(
+      "HTTP 500: Internal Server Error",
+    );
+  });
 });
diff --git a/src/agents/pi-embedded-helpers.sanitizeuserfacingtext.test.ts b/src/agents/pi-embedded-helpers.sanitizeuserfacingtext.test.ts
index df84dd6cd..9fac95b9c 100644
--- a/src/agents/pi-embedded-helpers.sanitizeuserfacingtext.test.ts
+++ b/src/agents/pi-embedded-helpers.sanitizeuserfacingtext.test.ts
@@ -19,12 +19,12 @@ describe("sanitizeUserFacingText", () => {
 
   it("sanitizes HTTP status errors with error hints", () => {
     expect(sanitizeUserFacingText("500 Internal Server Error")).toBe(
-      "The AI service returned an error. Please try again.",
+      "HTTP 500: Internal Server Error",
     );
   });
 
   it("sanitizes raw API error payloads", () => {
     const raw = '{"type":"error","error":{"message":"Something exploded","type":"server_error"}}';
-    expect(sanitizeUserFacingText(raw)).toBe("The AI service returned an error. Please try again.");
+    expect(sanitizeUserFacingText(raw)).toBe("LLM error server_error: Something exploded");
   });
 });
diff --git a/src/agents/pi-embedded-helpers/errors.ts b/src/agents/pi-embedded-helpers/errors.ts
index d29842958..e8fb7a4d1 100644
--- a/src/agents/pi-embedded-helpers/errors.ts
+++ b/src/agents/pi-embedded-helpers/errors.ts
@@ -201,6 +201,14 @@ export function formatRawAssistantErrorForUi(raw?: string): string {
   const trimmed = (raw ?? "").trim();
   if (!trimmed) return "LLM request failed with an unknown error.";
 
+  const httpMatch = trimmed.match(HTTP_STATUS_PREFIX_RE);
+  if (httpMatch) {
+    const rest = httpMatch[2].trim();
+    if (!rest.startsWith("{")) {
+      return `HTTP ${httpMatch[1]}: ${rest}`;
+    }
+  }
+
   const info = parseApiErrorInfo(trimmed);
   if (info?.message) {
     const prefix = info.httpCode ? `HTTP ${info.httpCode}` : "LLM error";
@@ -261,8 +269,8 @@ export function formatAssistantErrorText(
     return "The AI service is temporarily overloaded. Please try again in a moment.";
   }
 
-  if (isRawApiErrorPayload(raw)) {
-    return "The AI service returned an error. Please try again.";
+  if (isLikelyHttpErrorText(raw) || isRawApiErrorPayload(raw)) {
+    return formatRawAssistantErrorForUi(raw);
   }
 
   // Never return raw unhandled errors - log for debugging but return safe message
@@ -293,7 +301,7 @@ export function sanitizeUserFacingText(text: string): string {
   }
 
   if (isRawApiErrorPayload(trimmed) || isLikelyHttpErrorText(trimmed)) {
-    return "The AI service returned an error. Please try again.";
+    return formatRawAssistantErrorForUi(trimmed);
   }
 
   if (ERROR_PREFIX_RE.test(trimmed)) {
@@ -303,7 +311,7 @@ export function sanitizeUserFacingText(text: string): string {
     if (isTimeoutErrorMessage(trimmed)) {
       return "LLM request timed out.";
     }
-    return "The AI service returned an error. Please try again.";
+    return formatRawAssistantErrorForUi(trimmed);
   }
 
   return stripped;
diff --git a/src/agents/pi-embedded-runner/run/payloads.ts b/src/agents/pi-embedded-runner/run/payloads.ts
index be7ca41f5..005402775 100644
--- a/src/agents/pi-embedded-runner/run/payloads.ts
+++ b/src/agents/pi-embedded-runner/run/payloads.ts
@@ -6,6 +6,7 @@ import { formatToolAggregate } from "../../../auto-reply/tool-meta.js";
 import type { ClawdbotConfig } from "../../../config/config.js";
 import {
   formatAssistantErrorText,
+  formatRawAssistantErrorForUi,
   getApiErrorPayloadFingerprint,
   isRawApiErrorPayload,
   normalizeTextForComparison,
@@ -64,6 +65,12 @@ export function buildEmbeddedRunPayloads(params: {
   const rawErrorFingerprint = rawErrorMessage
     ? getApiErrorPayloadFingerprint(rawErrorMessage)
     : null;
+  const formattedRawErrorMessage = rawErrorMessage
+    ? formatRawAssistantErrorForUi(rawErrorMessage)
+    : null;
+  const normalizedFormattedRawErrorMessage = formattedRawErrorMessage
+    ? normalizeTextForComparison(formattedRawErrorMessage)
+    : null;
   const normalizedRawErrorText = rawErrorMessage
     ? normalizeTextForComparison(rawErrorMessage)
     : null;
@@ -116,10 +123,15 @@ export function buildEmbeddedRunPayloads(params: {
       if (trimmed === genericErrorText) return true;
     }
     if (rawErrorMessage && trimmed === rawErrorMessage) return true;
+    if (formattedRawErrorMessage && trimmed === formattedRawErrorMessage) return true;
     if (normalizedRawErrorText) {
       const normalized = normalizeTextForComparison(trimmed);
       if (normalized && normalized === normalizedRawErrorText) return true;
     }
+    if (normalizedFormattedRawErrorMessage) {
+      const normalized = normalizeTextForComparison(trimmed);
+      if (normalized && normalized === normalizedFormattedRawErrorMessage) return true;
+    }
     if (rawErrorFingerprint) {
       const fingerprint = getApiErrorPayloadFingerprint(trimmed);
       if (fingerprint && fingerprint === rawErrorFingerprint) return true;
diff --git a/src/gateway/assistant-identity.test.ts b/src/gateway/assistant-identity.test.ts
index 5085708e5..f966c7dc7 100644
--- a/src/gateway/assistant-identity.test.ts
+++ b/src/gateway/assistant-identity.test.ts
@@ -13,7 +13,9 @@ describe("resolveAssistantIdentity avatar normalization", () => {
       },
     };
 
-    expect(resolveAssistantIdentity({ cfg }).avatar).toBe(DEFAULT_ASSISTANT_IDENTITY.avatar);
+    expect(resolveAssistantIdentity({ cfg, workspaceDir: "" }).avatar).toBe(
+      DEFAULT_ASSISTANT_IDENTITY.avatar,
+    );
   });
 
   it("keeps short text avatars", () => {
@@ -25,7 +27,7 @@ describe("resolveAssistantIdentity avatar normalization", () => {
       },
     };
 
-    expect(resolveAssistantIdentity({ cfg }).avatar).toBe("PS");
+    expect(resolveAssistantIdentity({ cfg, workspaceDir: "" }).avatar).toBe("PS");
   });
 
   it("keeps path avatars", () => {
@@ -37,6 +39,6 @@ describe("resolveAssistantIdentity avatar normalization", () => {
       },
     };
 
-    expect(resolveAssistantIdentity({ cfg }).avatar).toBe("avatars/clawd.png");
+    expect(resolveAssistantIdentity({ cfg, workspaceDir: "" }).avatar).toBe("avatars/clawd.png");
   });
 });