diff --git a/web/src/connect.ts b/web/src/connect.ts
index 199f59a85..9a6d4cff4 100644
--- a/web/src/connect.ts
+++ b/web/src/connect.ts
@@ -1,7 +1,7 @@
 import { timestampDate } from "@bufbuild/protobuf/wkt";
 import { Code, ConnectError, createClient, type Interceptor } from "@connectrpc/connect";
 import { createConnectTransport } from "@connectrpc/connect-web";
-import { getAccessToken, isTokenExpired, REQUEST_TOKEN_EXPIRY_BUFFER_MS, setAccessToken } from "./auth-state";
+import { getAccessToken, hasStoredToken, isTokenExpired, REQUEST_TOKEN_EXPIRY_BUFFER_MS, setAccessToken } from "./auth-state";
 import { ActivityService } from "./types/proto/api/v1/activity_service_pb";
 import { AttachmentService } from "./types/proto/api/v1/attachment_service_pb";
 import { AuthService } from "./types/proto/api/v1/auth_service_pb";
@@ -124,7 +124,13 @@ async function refreshAndGetAccessToken(): Promise<string> {
 async function getRequestToken(): Promise<string | null> {
   let token = getAccessToken();
   if (!token) {
-    return null;
+    if (!hasStoredToken()) return null;
+    try {
+      token = await refreshAndGetAccessToken();
+    } catch {
+      return null;
+    }
+    return token;
   }
 
   // Preflight refresh: avoid sending requests with expired access tokens.
diff --git a/web/src/hooks/useTokenRefreshOnFocus.ts b/web/src/hooks/useTokenRefreshOnFocus.ts
index cab7575c7..f838087d0 100644
--- a/web/src/hooks/useTokenRefreshOnFocus.ts
+++ b/web/src/hooks/useTokenRefreshOnFocus.ts
@@ -1,5 +1,5 @@
 import { useEffect } from "react";
-import { FOCUS_TOKEN_EXPIRY_BUFFER_MS, getAccessToken, isTokenExpired } from "@/auth-state";
+import { FOCUS_TOKEN_EXPIRY_BUFFER_MS, hasStoredToken, isTokenExpired } from "@/auth-state";
 
 /**
  * Hook that proactively refreshes the access token when the tab becomes visible
@@ -20,9 +20,8 @@ export function useTokenRefreshOnFocus(refreshFn: () => Promise<void>, enabled:
         return;
       }
 
-      // Only refresh if we have a token
-      const token = getAccessToken();
-      if (!token) {
+      // Only refresh if the user has logged in before (token in localStorage)
+      if (!hasStoredToken()) {
         return;
       }