diff --git a/web/src/auth-state.ts b/web/src/auth-state.ts
index 74da7779a..e9f994805 100644
--- a/web/src/auth-state.ts
+++ b/web/src/auth-state.ts
@@ -61,11 +61,10 @@ export const getAccessToken = (): string | null => {
           accessToken = storedToken;
           tokenExpiresAt = expiresAt;
         }
-        // Do NOT remove expired tokens here. Callers such as InstanceContext.initialize()
-        // run concurrently with AuthContext.initialize() via Promise.all. If we eagerly
-        // delete the expired token from localStorage, hasStoredToken() (called synchronously
-        // inside AuthContext.initialize()) finds nothing and skips the refresh attempt,
-        // logging the user out even when the refresh-token cookie is still valid.
+        // Do NOT remove expired tokens here. getRequestToken() in connect.ts calls
+        // hasStoredToken() to decide whether to attempt a refresh — if we eagerly delete
+        // the expired token, it returns null immediately, skipping the refresh and sending
+        // the request without credentials.
         // clearAccessToken() handles proper cleanup after a confirmed auth failure or logout.
       }
     } catch (e) {
diff --git a/web/src/contexts/AuthContext.tsx b/web/src/contexts/AuthContext.tsx
index 0ce0741dd..943b4a207 100644
--- a/web/src/contexts/AuthContext.tsx
+++ b/web/src/contexts/AuthContext.tsx
@@ -1,7 +1,7 @@
 import { useQueryClient } from "@tanstack/react-query";
 import { createContext, type ReactNode, useCallback, useContext, useMemo, useState } from "react";
-import { clearAccessToken, hasStoredToken } from "@/auth-state";
-import { authServiceClient, shortcutServiceClient, userServiceClient } from "@/connect";
+import { clearAccessToken, getAccessToken } from "@/auth-state";
+import { authServiceClient, refreshAccessToken, shortcutServiceClient, userServiceClient } from "@/connect";
 import { userKeys } from "@/hooks/useUserQueries";
 import type { Shortcut } from "@/types/proto/api/v1/shortcut_service_pb";
 import type { User, UserSetting_GeneralSetting, UserSetting_WebhooksSetting } from "@/types/proto/api/v1/user_service_pb";
@@ -53,9 +53,21 @@ export function AuthProvider({ children }: { children: ReactNode }) {
   const initialize = useCallback(async () => {
     setState((prev) => ({ ...prev, isLoading: true }));
 
-    // If there is no stored token at all, the user is not authenticated.
-    // Skip the network call — there is nothing to refresh and no session to restore.
-    if (!hasStoredToken()) {
+    // Try to get or refresh the access token.
+    // This handles PWA isolated storage scenarios (e.g., iOS Safari) where localStorage
+    // may be empty but a valid HTTP-only refresh token cookie still exists.
+    // getAccessToken() returns a cached token or loads from localStorage if valid.
+    if (!getAccessToken()) {
+      try {
+        await refreshAccessToken();
+      } catch {
+        // Refresh failed - no valid session
+      }
+    }
+
+    // If we still don't have a token after refresh attempt, skip getCurrentUser call
+    // to avoid unnecessary network request for unauthenticated users.
+    if (!getAccessToken()) {
       setState({
         currentUser: undefined,
         userGeneralSetting: undefined,