diff --git a/web/src/lib/fetcher.ts b/web/src/lib/fetcher.ts
index 537ccd661b..d44ff3461a 100644
--- a/web/src/lib/fetcher.ts
+++ b/web/src/lib/fetcher.ts
@@ -33,6 +33,13 @@ const DEFAULT_AUTH_ERROR_MSG =
 
 const DEFAULT_ERROR_MSG = "An error occurred while fetching the data.";
 
+export function isAuthStatusError(error: unknown): boolean {
+  return (
+    error instanceof FetchError &&
+    (error.status === 401 || error.status === 402 || error.status === 403)
+  );
+}
+
 /**
  * SWR `onErrorRetry` callback that suppresses automatic retries for
  * auth or tier-gated errors (401/402/403). Pass this to any SWR hook whose
@@ -42,11 +49,7 @@ const DEFAULT_ERROR_MSG = "An error occurred while fetching the data.";
 export const skipRetryOnAuthError: NonNullable<
   import("swr").SWRConfiguration["onErrorRetry"]
 > = (error, _key, _config, revalidate, { retryCount }) => {
-  if (
-    error instanceof FetchError &&
-    (error.status === 401 || error.status === 402 || error.status === 403)
-  )
-    return;
+  if (isAuthStatusError(error)) return;
   // For non-auth errors, retry with exponential backoff
   if (
     _config.errorRetryCount !== undefined &&
diff --git a/web/src/providers/UserProvider.test.tsx b/web/src/providers/UserProvider.test.tsx
new file mode 100644
index 0000000000..513241de87
--- /dev/null
+++ b/web/src/providers/UserProvider.test.tsx
@@ -0,0 +1,172 @@
+// Guards the /api/me contract: unresolved reads as loading and failed auth fetches self-heal.
+import { act, render, screen } from "@tests/setup/test-utils";
+// Relative import: jest's moduleNameMapper swaps the @/ path for the global stub.
+import { UserProvider, useUser } from "./UserProvider";
+import { FetchError } from "@/lib/fetcher";
+import { useCurrentUser } from "@/lib/users/hooks";
+import { User } from "@/lib/types";
+
+jest.mock("posthog-js/react", () => ({ usePostHog: () => undefined }));
+jest.mock("@/lib/settings/hooks", () => ({ useSettings: () => ({}) }));
+jest.mock("@/lib/users/hooks", () => ({ useCurrentUser: jest.fn() }));
+jest.mock("@/lib/auth/hooks", () => ({
+  useAuthTypeMetadata: () => ({
+    authTypeMetadata: undefined,
+    isLoading: false,
+  }),
+  useTokenRefresh: jest.fn(),
+}));
+jest.mock("@/lib/users/svc", () => ({
+  updateUserPersonalization: jest.fn(),
+  setUserDefaultModel: jest.fn(),
+}));
+jest.mock("next-themes", () => ({
+  useTheme: () => ({ theme: "light", setTheme: jest.fn() }),
+}));
+
+const mockedUseCurrentUser = jest.mocked(useCurrentUser);
+
+function setCurrentUser(overrides: Partial<ReturnType<typeof useCurrentUser>>) {
+  mockedUseCurrentUser.mockReturnValue({
+    user: undefined,
+    isLoading: true,
+    mutateUser: jest.fn(),
+    userError: undefined,
+    ...overrides,
+  } as ReturnType<typeof useCurrentUser>);
+}
+
+function Probe() {
+  const { user, userResolution } = useUser();
+  if (userResolution !== "resolved") {
+    return <span>{userResolution}</span>;
+  }
+  return <span>{user ? user.email : "signed-out"}</span>;
+}
+
+// Factory: an identical element reference would let React skip the re-render.
+function probeTree() {
+  return (
+    <UserProvider>
+      <Probe />
+    </UserProvider>
+  );
+}
+
+function renderProbe() {
+  return render(probeTree());
+}
+
+describe("UserProvider user resolution", () => {
+  it("reports loading while /api/me is unresolved", () => {
+    setCurrentUser({ user: undefined });
+    renderProbe();
+    expect(screen.getByText("loading")).toBeInTheDocument();
+  });
+
+  it("reports loading when /api/me failed instead of signed-out", () => {
+    setCurrentUser({
+      user: undefined,
+      isLoading: false,
+      userError: new Error("transient"),
+    });
+    renderProbe();
+    expect(screen.getByText("loading")).toBeInTheDocument();
+  });
+
+  it("reports signed-out only for a resolved null user", () => {
+    setCurrentUser({ user: null, isLoading: false });
+    renderProbe();
+    expect(screen.getByText("signed-out")).toBeInTheDocument();
+  });
+
+  it("exposes the user once resolved", () => {
+    setCurrentUser({
+      user: { id: "u1", email: "john@example.com" } as User,
+      isLoading: false,
+    });
+    renderProbe();
+    expect(screen.getByText("john@example.com")).toBeInTheDocument();
+  });
+});
+
+function authError(label: string): FetchError {
+  return new FetchError(label, 403, null);
+}
+
+describe("UserProvider /api/me retry", () => {
+  beforeEach(() => {
+    jest.useFakeTimers();
+  });
+
+  afterEach(() => {
+    jest.useRealTimers();
+  });
+
+  it("retries an auth failure on a backoff schedule, then reports unavailable", () => {
+    const mutateUser = jest.fn();
+
+    setCurrentUser({ userError: authError("fail 1"), mutateUser });
+    const { rerender } = renderProbe();
+    act(() => jest.advanceTimersByTime(2_000));
+    expect(mutateUser).toHaveBeenCalledTimes(1);
+
+    setCurrentUser({ userError: authError("fail 2"), mutateUser });
+    rerender(probeTree());
+    act(() => jest.advanceTimersByTime(5_000));
+    expect(mutateUser).toHaveBeenCalledTimes(2);
+
+    setCurrentUser({ userError: authError("fail 3"), mutateUser });
+    rerender(probeTree());
+    act(() => jest.advanceTimersByTime(15_000));
+    expect(mutateUser).toHaveBeenCalledTimes(3);
+
+    setCurrentUser({ userError: authError("fail 4"), mutateUser });
+    rerender(probeTree());
+    act(() => jest.advanceTimersByTime(120_000));
+    expect(mutateUser).toHaveBeenCalledTimes(3);
+    // Budget spent: unavailable, never a false signed-out claim.
+    expect(screen.getByText("unavailable")).toBeInTheDocument();
+  });
+
+  it("does not schedule retries for non-auth failures (SWR owns those)", () => {
+    const mutateUser = jest.fn();
+
+    setCurrentUser({
+      userError: new FetchError("boom", 500, null),
+      mutateUser,
+    });
+    renderProbe();
+    act(() => jest.advanceTimersByTime(29_000));
+    expect(mutateUser).not.toHaveBeenCalled();
+    expect(screen.getByText("loading")).toBeInTheDocument();
+  });
+
+  it("reports unavailable once a non-auth failure outlives the deadline", () => {
+    setCurrentUser({ userError: new FetchError("boom", 500, null) });
+    renderProbe();
+    act(() => jest.advanceTimersByTime(31_000));
+    expect(screen.getByText("unavailable")).toBeInTheDocument();
+  });
+
+  it("resets the retry budget after a successful fetch", () => {
+    const mutateUser = jest.fn();
+
+    setCurrentUser({ userError: authError("fail"), mutateUser });
+    const { rerender } = renderProbe();
+    act(() => jest.advanceTimersByTime(2_000));
+    expect(mutateUser).toHaveBeenCalledTimes(1);
+
+    setCurrentUser({
+      user: { id: "u1", email: "john@example.com" } as User,
+      isLoading: false,
+      mutateUser,
+    });
+    rerender(probeTree());
+
+    setCurrentUser({ userError: authError("fail again"), mutateUser });
+    rerender(probeTree());
+    act(() => jest.advanceTimersByTime(2_000));
+    expect(mutateUser).toHaveBeenCalledTimes(2);
+  });
+});
diff --git a/web/src/providers/UserProvider.tsx b/web/src/providers/UserProvider.tsx
index 2950afe454..dd5094480a 100644
--- a/web/src/providers/UserProvider.tsx
+++ b/web/src/providers/UserProvider.tsx
@@ -16,6 +16,7 @@ import {
   ThemePreference,
 } from "@/lib/types";
 import { usePostHog } from "posthog-js/react";
+import { isAuthStatusError } from "@/lib/fetcher";
 import { useSettings } from "@/lib/settings/hooks";
 import { useCurrentUser } from "@/lib/users/hooks";
 import { useAuthTypeMetadata, useTokenRefresh } from "@/lib/auth/hooks";
@@ -26,8 +27,18 @@ import {
 } from "@/lib/users/svc";
 import { useTheme } from "next-themes";
 
+// Auth failures skip SWR's retry but are usually transient refresh races. SWR's backoff owns the rest.
+const ME_RETRY_DELAYS_MS = [2_000, 5_000, 15_000];
+
+// Ceiling on reporting loading for a failing /api/me, so the account menu always comes back.
+const ME_LOADING_DEADLINE_MS = 30_000;
+
+/** Only "resolved" lets a null user mean signed out. "unavailable" means /api/me keeps failing for a possibly valid session. */
+export type UserResolution = "loading" | "unavailable" | "resolved";
+
 interface UserContextType {
   user: User | null;
+  userResolution: UserResolution;
   isAdmin: boolean;
   isCurator: boolean;
   refreshUser: () => Promise<void>;
@@ -61,7 +72,7 @@ interface UserContextType {
 const UserContext = createContext<UserContextType | undefined>(undefined);
 
 export function UserProvider({ children }: { children: React.ReactNode }) {
-  const { user: fetchedUser, mutateUser } = useCurrentUser();
+  const { user: fetchedUser, mutateUser, userError } = useCurrentUser();
   const { authTypeMetadata, isLoading: authTypeMetadataLoading } =
     useAuthTypeMetadata();
   const updatedSettingsData = useSettings();
@@ -99,6 +110,55 @@ export function UserProvider({ children }: { children: React.ReactNode }) {
     setUpToDateUser(mergeUserPreferences(fetchedUser ?? null));
   }, [fetchedUser, mergeUserPreferences]);
 
+  const [meRetriesExhausted, setMeRetriesExhausted] = useState(false);
+
+  const meRetryCountRef = useRef(0);
+  const meFirstErrorAtRef = useRef<number | null>(null);
+  useEffect(() => {
+    if (!userError) {
+      meRetryCountRef.current = 0;
+      meFirstErrorAtRef.current = null;
+      setMeRetriesExhausted(false);
+      return;
+    }
+    meFirstErrorAtRef.current ??= Date.now();
+    if (!isAuthStatusError(userError)) {
+      // SWR's backoff owns non-auth retries. Bound only how long we report loading.
+      const remaining =
+        ME_LOADING_DEADLINE_MS - (Date.now() - meFirstErrorAtRef.current);
+      if (remaining <= 0) {
+        setMeRetriesExhausted(true);
+        return;
+      }
+      const deadlineId = setTimeout(
+        () => setMeRetriesExhausted(true),
+        remaining
+      );
+      return () => clearTimeout(deadlineId);
+    }
+    // Fresh error identity per failure advances the schedule. The count moves in the timer, so StrictMode is safe.
+    const attempt = meRetryCountRef.current;
+    const delay = ME_RETRY_DELAYS_MS[attempt];
+    if (delay === undefined) {
+      setMeRetriesExhausted(true);
+      return;
+    }
+    const timeoutId = setTimeout(() => {
+      meRetryCountRef.current = attempt + 1;
+      void mutateUser();
+    }, delay);
+    return () => clearTimeout(timeoutId);
+  }, [userError, mutateUser]);
+
+  const awaitingMe = fetchedUser === undefined && !meRetriesExhausted;
+  const mergePending = fetchedUser != null && upToDateUser === null;
+  const userResolution: UserResolution =
+    awaitingMe || mergePending
+      ? "loading"
+      : fetchedUser === undefined
+        ? "unavailable"
+        : "resolved";
+
   useEffect(() => {
     if (!posthog) return;
 
@@ -539,6 +599,7 @@ export function UserProvider({ children }: { children: React.ReactNode }) {
     <UserContext.Provider
       value={{
         user: upToDateUser,
+        userResolution,
         refreshUser,
         authTypeMetadata,
         updateUserAutoScroll,
diff --git a/web/src/refresh-components/skeletons/SidebarTabSkeleton.tsx b/web/src/refresh-components/skeletons/SidebarTabSkeleton.tsx
index 36d3e1db9a..79eb9f58ea 100644
--- a/web/src/refresh-components/skeletons/SidebarTabSkeleton.tsx
+++ b/web/src/refresh-components/skeletons/SidebarTabSkeleton.tsx
@@ -2,18 +2,20 @@ import { cn } from "@opal/utils";
 
 interface SidebarTabSkeletonProps {
   textWidth?: string;
+  folded?: boolean;
 }
 
 export default function SidebarTabSkeleton({
   textWidth = "w-2/3",
+  folded,
 }: SidebarTabSkeletonProps) {
   return (
     <div className="w-full rounded-08 p-1.5">
       <div className="h-6 flex flex-row items-center px-1 py-0.5">
         <div
           className={cn(
-            "h-3 rounded-sm bg-background-tint-04 animate-pulse",
-            textWidth
+            "bg-background-tint-04 animate-pulse",
+            folded ? "h-4 w-4 rounded-full" : cn("h-3 rounded-sm", textWidth)
           )}
         />
       </div>
diff --git a/web/src/sections/sidebar/AccountPopover.test.tsx b/web/src/sections/sidebar/AccountPopover.test.tsx
new file mode 100644
index 0000000000..caec42688a
--- /dev/null
+++ b/web/src/sections/sidebar/AccountPopover.test.tsx
@@ -0,0 +1,76 @@
+// The chip shows a skeleton while unresolved and "Anonymous" only when resolved signed-out.
+import { render, screen } from "@tests/setup/test-utils";
+import AccountPopover from "@/sections/sidebar/AccountPopover";
+import { useUser } from "@/providers/UserProvider";
+import { User } from "@/lib/types";
+
+// Factory mock: the global stub pins userResolution to "resolved".
+jest.mock("@/providers/UserProvider", () => ({ useUser: jest.fn() }));
+jest.mock("next/navigation", () => ({
+  useRouter: () => ({ push: jest.fn() }),
+  usePathname: () => "/app",
+  useSearchParams: () => new URLSearchParams(),
+}));
+jest.mock("@/sections/sidebar/NotificationsPopover", () => ({
+  __esModule: true,
+  default: () => null,
+}));
+jest.mock("@/hooks/useAppFocus", () => ({
+  __esModule: true,
+  default: () => ({ isUserSettings: () => false }),
+}));
+jest.mock("@/hooks/useScreenSize", () => ({
+  __esModule: true,
+  default: () => ({ isMobile: false }),
+}));
+jest.mock("@/lib/settings/hooks", () => ({
+  useSettings: () => ({ vectorDbEnabled: false }),
+}));
+jest.mock("@/hooks/useNotifications", () => ({
+  useNotificationSummary: () => ({ undismissedCount: 0, refresh: jest.fn() }),
+}));
+
+const mockedUseUser = jest.mocked(useUser);
+
+function setUser(
+  user: User | null,
+  userResolution: "loading" | "unavailable" | "resolved"
+) {
+  mockedUseUser.mockReturnValue({
+    user,
+    userResolution,
+  } as ReturnType<typeof useUser>);
+}
+
+it("shows a skeleton instead of Anonymous while the user is unresolved", () => {
+  setUser(null, "loading");
+  render(<AccountPopover />);
+  expect(screen.queryByText("Anonymous")).not.toBeInTheDocument();
+  expect(screen.queryByRole("button")).not.toBeInTheDocument();
+});
+
+it("shows a neutral label, not Anonymous, when the user is unavailable", () => {
+  setUser(null, "unavailable");
+  render(<AccountPopover />);
+  expect(screen.getByText("Account")).toBeInTheDocument();
+  expect(screen.queryByText("Anonymous")).not.toBeInTheDocument();
+});
+
+it("shows Anonymous for a resolved signed-out user", () => {
+  setUser(null, "resolved");
+  render(<AccountPopover />);
+  expect(screen.getByText("Anonymous")).toBeInTheDocument();
+});
+
+it("shows the user's name once resolved", () => {
+  setUser(
+    {
+      id: "u1",
+      email: "john@example.com",
+      personalization: { name: "John" },
+    } as unknown as User,
+    "resolved"
+  );
+  render(<AccountPopover />);
+  expect(screen.getByText("John")).toBeInTheDocument();
+});
diff --git a/web/src/sections/sidebar/AccountPopover.tsx b/web/src/sections/sidebar/AccountPopover.tsx
index a486aeaebd..58fcde4186 100644
--- a/web/src/sections/sidebar/AccountPopover.tsx
+++ b/web/src/sections/sidebar/AccountPopover.tsx
@@ -30,6 +30,7 @@ import useAppFocus from "@/hooks/useAppFocus";
 import useScreenSize from "@/hooks/useScreenSize";
 import { useSettings } from "@/lib/settings/hooks";
 import UserAvatar from "@/refresh-components/avatars/UserAvatar";
+import SidebarTabSkeleton from "@/refresh-components/skeletons/SidebarTabSkeleton";
 import { useNotificationSummary } from "@/hooks/useNotifications";
 import { SvgOnyxLogo } from "@opal/logos";
 import { markdown } from "@opal/utils";
@@ -45,7 +46,7 @@ function SettingsPopover({
   onOpenNotifications,
   undismissedCount,
 }: SettingsPopoverProps) {
-  const { user } = useUser();
+  const { user, userResolution } = useUser();
   const settings = useSettings();
   const enterpriseSettings = settings.enterprise;
   const router = useRouter();
@@ -90,7 +91,14 @@ function SettingsPopover({
     <PopoverMenu>
       {[
         <div key="user-email" className="p-2">
-          <Content sizePreset="main-ui" title={getUserEmail(user)} />
+          <Content
+            sizePreset="main-ui"
+            title={
+              userResolution === "unavailable"
+                ? "Profile unavailable"
+                : getUserEmail(user)
+            }
+          />
         </div>,
         null,
         <div key="user-settings" data-testid="Settings/user-settings">
@@ -198,13 +206,14 @@ export default function AccountPopover({
   const [popupState, setPopupState] = useState<
     "Settings" | "Notifications" | undefined
   >(undefined);
-  const { user } = useUser();
+  const { user, userResolution } = useUser();
   const appFocus = useAppFocus();
   const { isMobile } = useScreenSize();
   const { vectorDbEnabled } = useSettings();
   const { undismissedCount, refresh: refreshNotificationSummary } =
     useNotificationSummary();
-  const userDisplayName = getUserDisplayName(user);
+  const userDisplayName =
+    userResolution === "unavailable" ? "Account" : getUserDisplayName(user);
 
   const handlePopoverOpen = (state: boolean) => {
     if (state) {
@@ -221,6 +230,9 @@ export default function AccountPopover({
       setPopupState(undefined);
     }
   };
+  if (userResolution === "loading") {
+    return <SidebarTabSkeleton folded={folded} />;
+  }
 
   return (
     <Popover open={!!popupState} onOpenChange={handlePopoverOpen}>
diff --git a/web/tests/setup/mocks/components/UserProvider.tsx b/web/tests/setup/mocks/components/UserProvider.tsx
index ccf8d652cb..e4916f20c7 100644
--- a/web/tests/setup/mocks/components/UserProvider.tsx
+++ b/web/tests/setup/mocks/components/UserProvider.tsx
@@ -19,6 +19,7 @@ import React, { createContext, useContext } from "react";
 
 interface UserContextType {
   user: any;
+  userResolution: "loading" | "unavailable" | "resolved";
   isAdmin: boolean;
   isCurator: boolean;
   refreshUser: () => Promise<void>;
@@ -36,6 +37,7 @@ interface UserContextType {
 
 const mockUserContext: UserContextType = {
   user: null,
+  userResolution: "resolved",
   isAdmin: false,
   isCurator: false,
   refreshUser: async () => {},