Issue
When signing in from the Box Drive login screen, authentication may not complete and the same login screen may appear again. The main symptoms are as follows:
- Authentication does not complete after signing in from the Box Drive login screen.
- The login screen does not close after sign-in, and the same login screen appears again.
- The Box icon in the notification area is grayed out.
- Uninstalling and reinstalling Box Drive does not resolve the issue.
Root Cause
The primary cause of this issue is a timeout in proxy-based communication when Box Drive attempts to connect to Box.
Communication with /oauth2/token fails, preventing the authentication process from completing. As a result, the login information cannot be saved correctly, causing the login dialog to remain open or appear again.
In particular, if the logs contain ConnectTimeoutError, the proxy may be blocking connections to the required destinations.
Resolution
1. Open the Box Drive log file
Open the .log file that starts with Box-, and check the entries recorded around the time when the issue occurred.
2. Check whether any timeout entries are recorded
Specifically, check whether the log contains entries such as the following:
ConnectTimeoutError- Timeout while connecting to
api.box.com - Failed POST to
/oauth2/token
Examples:
2025-11-21 17:08:00.268 35068 INFO CompleteAuthenticati network_layer Request: POST https://api.box.com/oauth2/token {} {'Priority': 'u=2'}
2025-11-21 17:08:21.325 35068 INFO CompleteAuthenticati network_layer Got a ConnectTimeout so calling refresh_proxy_settings: ProxyAuthHTTPSConnectionPool(host='api.box.com', port=443): Max retries exceeded with url: /oauth2/token (Caused by ConnectTimeoutError(<box.util.proxy_auth_https_connection.ProxyAuthHTTPSConnection object at 0x000002386CA6B2C0>, 'Connection to xxxx.xxx.jp timed out. (connect timeout=180)'))3. Check the proxy settings
If timeout entries are recorded, check the proxy settings on the affected machine.
- Whether the machine can connect to the proxy server correctly
- Whether there are no errors in the proxy settings
- Whether internal network restrictions are not affecting the connection
4. Check whether the destinations required by Box are allowed
Check whether the proxy or firewall allows communication with the hosts required by Box. Refer to the following support information as needed.
If the issue persists
If the issue is not resolved after performing the steps above, contact Box Support and provide the following information:
- Box Drive version
- Date and time when the issue occurred
- Whether a proxy environment is used
- Box Drive logs around the time when the issue occurred (For information on how to submit Box Drive logs: https://support.box.com/hc/en-us/articles/360044193913)