fix(web): extend bestEffort to conversation history and settings daemon calls

apps/web/src/domains/chat/hooks/use-conversation-history.ts

@@ -310,6 +310,7 @@ export function useConversationHistory({
       context: isOlderPageError
         ? "conversation_history_older_page"
         : "conversation_history_initial",
+      bestEffort: true,
     });
 
     if (!isOlderPageError) {

apps/web/src/domains/settings/ai/web-search-card.tsx

@@ -125,7 +125,7 @@ export function WebSearchCard() {
       } catch (error) {
         if (cancelled) return;
         setWebSearchHasStoredKey(false);
-        captureError(error, { context: "settings-ai-web-search-read-secret" });
+        captureError(error, { context: "settings-ai-web-search-read-secret", bestEffort: true });
       }
     })();
 

apps/web/src/lib/sentry/capture-error.test.ts

@@ -186,14 +186,109 @@ describe("isExpectedDaemonTransientError", () => {
     ).toBe(false);
   });
 
-  test("returns false for non-ApiError instances", () => {
+  test("returns false for non-ApiError Error instances", () => {
     expect(isExpectedDaemonTransientError(new Error("random error"))).toBe(
       false,
     );
     expect(
       isExpectedDaemonTransientError(new TypeError("Failed to fetch")),
     ).toBe(false);
+  });
+
+  test("returns false for primitives and null", () => {
     expect(isExpectedDaemonTransientError("string error")).toBe(false);
     expect(isExpectedDaemonTransientError(null)).toBe(false);
+    expect(isExpectedDaemonTransientError(undefined)).toBe(false);
+    expect(isExpectedDaemonTransientError(42)).toBe(false);
+  });
+
+  // HeyAPI throwOnError throws raw JSON response bodies ({detail: "..."})
+  // without wrapping in ApiError. These tests verify detection of the raw
+  // Django REST framework error shape.
+  test("returns true for raw {detail} with 503 startup message", () => {
+    expect(
+      isExpectedDaemonTransientError({
+        detail: "Your assistant is still starting up. Please try again in a moment.",
+      }),
+    ).toBe(true);
+  });
+
+  test("returns true for raw {detail} with org-header message", () => {
+    expect(
+      isExpectedDaemonTransientError({
+        detail: "Vellum-Organization-Id header is required.",
+      }),
+    ).toBe(true);
+  });
+
+  test("returns true for raw {detail} with 401 auth message", () => {
+    expect(
+      isExpectedDaemonTransientError({
+        detail: "Authentication credentials were not provided.",
+      }),
+    ).toBe(true);
+  });
+
+  test("returns true for raw {detail} with bad gateway message", () => {
+    expect(
+      isExpectedDaemonTransientError({ detail: "Bad gateway" }),
+    ).toBe(true);
+    expect(
+      isExpectedDaemonTransientError({ detail: "Bad Gateway" }),
+    ).toBe(true);
+  });
+
+  test("returns false for raw {detail} with unknown message", () => {
+    expect(
+      isExpectedDaemonTransientError({ detail: "Internal Server Error" }),
+    ).toBe(false);
+    expect(
+      isExpectedDaemonTransientError({ detail: "Permission denied." }),
+    ).toBe(false);
+  });
+
+  test("returns false for raw object without detail field", () => {
+    expect(
+      isExpectedDaemonTransientError({ message: "something" }),
+    ).toBe(false);
+    expect(isExpectedDaemonTransientError({})).toBe(false);
+  });
+
+  test("returns false for raw {detail} with non-string value", () => {
+    expect(
+      isExpectedDaemonTransientError({ detail: 503 }),
+    ).toBe(false);
+    expect(
+      isExpectedDaemonTransientError({ detail: ["error1", "error2"] }),
+    ).toBe(false);
+  });
+});
+
+describe("captureError with bestEffort and raw HeyAPI errors", () => {
+  test("silently drops raw {detail} daemon transient errors with bestEffort", () => {
+    captureExceptionMock.mockClear();
+    captureError(
+      { detail: "Your assistant is still starting up. Please try again in a moment." },
+      { context: "test-ctx", bestEffort: true },
+    );
+    expect(captureExceptionMock).not.toHaveBeenCalled();
+  });
+
+  test("reports raw {detail} daemon transient errors without bestEffort", () => {
+    captureExceptionMock.mockClear();
+    captureError(
+      { detail: "Your assistant is still starting up." },
+      { context: "test-ctx" },
+    );
+    expect(captureExceptionMock).toHaveBeenCalledTimes(1);
+  });
+
+  test("reports raw {detail} with unknown message even with bestEffort", () => {
+    captureExceptionMock.mockClear();
+    captureError(
+      { detail: "Internal Server Error" },
+      { context: "test-ctx", bestEffort: true },
+    );
+    expect(captureExceptionMock).toHaveBeenCalledTimes(1);
   });
 });

apps/web/src/lib/sentry/capture-error.ts

@@ -46,6 +46,21 @@ export function normalizeToError(value: unknown): Error {
   return new Error(String(value));
 }
 
+/**
+ * Known daemon transient detail messages. HeyAPI's `throwOnError`
+ * throws the raw JSON body (`{detail: "..."}`) without the HTTP status
+ * code, so we fall back to substring matching on the `detail` value.
+ *
+ * Each entry is a lowercase substring that uniquely identifies one of
+ * the daemon's expected transient responses.
+ */
+const DAEMON_TRANSIENT_DETAILS: readonly string[] = [
+  "still starting up",            // 503 — daemon booting
+  "organization-id header",       // 400 — org store not hydrated
+  "authentication credentials",   // 401 — auth session race
+  "bad gateway",                  // 502 — reverse proxy
+];
+
 /**
  * Detects expected transient HTTP errors from daemon API calls that
  * occur during normal startup sequences and auth-session hydration.
@@ -59,21 +74,37 @@ export function normalizeToError(value: unknown): Error {
  * - **400 with org-header message** — Org store has not hydrated yet;
  *   the `Vellum-Organization-Id` header interceptor read `null`
  *
- * Only `ApiError` instances are matched. Other error types (TypeError,
- * generic Error, plain objects) pass through — they represent network
- * failures (handled by `isTransientNetworkError`) or application bugs.
+ * Matches both structured `ApiError` instances (from manual
+ * construction with `throwOnError: false`) and raw `{detail: string}`
+ * objects thrown by HeyAPI's `throwOnError: true`.
+ *
+ * Reference: https://heyapi.dev/openapi-ts/clients/fetch#throwing-errors
  */
 export function isExpectedDaemonTransientError(error: unknown): boolean {
-  if (!(error instanceof ApiError)) return false;
-  if (error.status === 503) return true;
-  if (error.status === 502) return true;
-  if (error.status === 401) return true;
-  if (
-    error.status === 400 &&
-    error.message.includes("Organization-Id header")
-  ) {
-    return true;
+  if (error instanceof ApiError) {
+    if (error.status === 503) return true;
+    if (error.status === 502) return true;
+    if (error.status === 401) return true;
+    if (
+      error.status === 400 &&
+      error.message.includes("Organization-Id header")
+    ) {
+      return true;
+    }
+    return false;
+  }
+
+  // HeyAPI throwOnError throws the raw JSON response body — typically
+  // {detail: "message"} for Django REST framework errors — without the
+  // HTTP status code. Match on known daemon transient detail strings.
+  if (typeof error === "object" && error !== null && "detail" in error) {
+    const detail = (error as Record<string, unknown>).detail;
+    if (typeof detail === "string") {
+      const lower = detail.toLowerCase();
+      return DAEMON_TRANSIENT_DETAILS.some((pattern) => lower.includes(pattern));
+    }
   }
+
   return false;
 }