diff --git a/web/src/auth-state.ts b/web/src/auth-state.ts
index d070bc992..058b96900 100644
--- a/web/src/auth-state.ts
+++ b/web/src/auth-state.ts
@@ -54,10 +54,12 @@ export const setAccessToken = (token: string | null, expiresAt?: Date): void =>
   }
 };
 
-export const isTokenExpired = (): boolean => {
+export const isTokenExpired = (bufferMs: number = 30000): boolean => {
   if (!tokenExpiresAt) return true;
-  // Consider expired 30 seconds before actual expiry for safety
-  return new Date() >= new Date(tokenExpiresAt.getTime() - 30000);
+  // Consider expired with a safety buffer before actual expiry
+  // Default: 30 seconds for regular requests
+  // Can use longer buffer (e.g., 2 minutes) for proactive refresh
+  return new Date() >= new Date(tokenExpiresAt.getTime() - bufferMs);
 };
 
 export const clearAccessToken = (): void => {
diff --git a/web/src/connect.ts b/web/src/connect.ts
index 1a8cb7177..622b086b4 100644
--- a/web/src/connect.ts
+++ b/web/src/connect.ts
@@ -67,7 +67,7 @@ const refreshTransport = createConnectTransport({
 
 const refreshAuthClient = createClient(AuthService, refreshTransport);
 
-async function refreshAccessToken(): Promise<void> {
+export async function refreshAccessToken(): Promise<void> {
   const response = await refreshAuthClient.refreshToken({});
 
   if (!response.accessToken) {
diff --git a/web/src/hooks/useTokenRefreshOnFocus.ts b/web/src/hooks/useTokenRefreshOnFocus.ts
new file mode 100644
index 000000000..e6f2d406e
--- /dev/null
+++ b/web/src/hooks/useTokenRefreshOnFocus.ts
@@ -0,0 +1,51 @@
+import { useEffect } from "react";
+import { getAccessToken, isTokenExpired } from "@/auth-state";
+
+/**
+ * Hook that proactively refreshes the access token when the tab becomes visible
+ * and the token is expired or expiring soon.
+ *
+ * This prevents React Query's automatic refetch-on-window-focus from triggering
+ * multiple 401 errors when the user returns to the tab after the token has expired.
+ *
+ * Related issue: https://github.com/usememos/memos/issues/5589
+ */
+export function useTokenRefreshOnFocus(refreshFn: () => Promise<void>, enabled: boolean = true) {
+  useEffect(() => {
+    if (!enabled) return;
+
+    const handleVisibilityChange = async () => {
+      // Only act when tab becomes visible
+      if (document.visibilityState !== "visible") {
+        return;
+      }
+
+      // Only refresh if we have a token
+      const token = getAccessToken();
+      if (!token) {
+        return;
+      }
+
+      // Check if token is expired or expiring soon (within 2 minutes)
+      // Use a longer buffer than normal requests to be proactive
+      const bufferMs = 2 * 60 * 1000; // 2 minutes
+      if (isTokenExpired(bufferMs)) {
+        try {
+          console.debug("[useTokenRefreshOnFocus] Token expired/expiring, refreshing before queries refetch");
+          await refreshFn();
+          console.debug("[useTokenRefreshOnFocus] Token refreshed successfully");
+        } catch (error) {
+          // Don't block - let the normal auth interceptor handle it
+          // The user will be redirected if refresh fails
+          console.error("[useTokenRefreshOnFocus] Failed to refresh token:", error);
+        }
+      }
+    };
+
+    document.addEventListener("visibilitychange", handleVisibilityChange);
+
+    return () => {
+      document.removeEventListener("visibilitychange", handleVisibilityChange);
+    };
+  }, [refreshFn, enabled]);
+}
diff --git a/web/src/main.tsx b/web/src/main.tsx
index b3599aa43..5d617b210 100644
--- a/web/src/main.tsx
+++ b/web/src/main.tsx
@@ -8,9 +8,11 @@ import { RouterProvider } from "react-router-dom";
 import "./i18n";
 import "./index.css";
 import { ErrorBoundary } from "@/components/ErrorBoundary";
+import { refreshAccessToken } from "@/connect";
 import { AuthProvider, useAuth } from "@/contexts/AuthContext";
 import { InstanceProvider, useInstance } from "@/contexts/InstanceContext";
 import { ViewProvider } from "@/contexts/ViewContext";
+import { useTokenRefreshOnFocus } from "@/hooks/useTokenRefreshOnFocus";
 import { queryClient } from "@/lib/query-client";
 import router from "./router";
 import { applyLocaleEarly } from "./utils/i18n";
@@ -24,7 +26,7 @@ applyLocaleEarly();
 
 // Inner component that initializes contexts
 function AppInitializer({ children }: { children: React.ReactNode }) {
-  const { isInitialized: authInitialized, initialize: initAuth } = useAuth();
+  const { isInitialized: authInitialized, initialize: initAuth, currentUser } = useAuth();
   const { isInitialized: instanceInitialized, initialize: initInstance } = useInstance();
   const initStartedRef = useRef(false);
 
@@ -39,6 +41,11 @@ function AppInitializer({ children }: { children: React.ReactNode }) {
     init();
   }, [initAuth, initInstance]);
 
+  // Proactively refresh token on window focus to prevent 401 errors
+  // Only enabled when user is authenticated
+  // Related: https://github.com/usememos/memos/issues/5589
+  useTokenRefreshOnFocus(refreshAccessToken, !!currentUser);
+
   if (!authInitialized || !instanceInitialized) {
     return null;
   }