Azure VPN Gateway
An Azure service that enables the connection of on-premises networks to Azure through site-to-site virtual private networks.
1,778 questions
Azure VPN connection dropping and reconnecting
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James Sefton
0
Reputation points
Hi, we are experiencing issues where users are disconnected from the VPN and then it may reconnect itself a minute later.
If it does not, it will be stuck in reconciling state until the machine is restarted. Repairing, resetting and re-installing the application does not work also.
Any help would be appreciated.
Thanks,
James
Azure VPN Gateway
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Ganesh Patapati 6,830 Reputation points Microsoft External Staff Moderator2025-06-18T17:52:22.9966667+00:00 Hello James Sefton
The reason might be the current refresh token in the Azure VPN client, acquired from Entra ID, has expired or become invalid. This token is renewed approximately every hour. Entra tenant administrators can extend the sign-in frequency by adding conditional access policies. Please work with your Entra tenant administrators to extend the refresh token expiration interval. For your reference: https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-vpn-faq#vpn-disconnect
Looks like the updated version (3.4.0.0) might be the reason for this issue. Please refer: https://learn.microsoft.com/en-us/azure/vpn-gateway/azure-vpn-client-versions#azure-vpn-client---windows
If you are getting any of the below error, you need to reconnect. This triggers an interactive sign-in process in Microsoft Entra that issues a new refresh token and access token.
Your authentication with Microsoft Entra is expired. You need to re-authenticate in Entra to acquire a new token. Authentication timeout can be tuned by your administrator.orYour authentication with Microsoft Entra has expired so you need to re-authenticate to acquire a new token. Please try connecting again. Authentication policies and timeout are configured by your administrator in Entra tenant.For your reference: https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-troubleshoot-vpn-point-to-site-connection-problems#cause-15The refresh token can show as expired/invalid due to several reasons. You can check User Entra sign-in logs for debugging. For your reference: https://learn.microsoft.com/en-us/entra/identity/monitoring-health/concept-sign-ins
Refresh tokens can be revoked at any time, because of timeouts and revocations. Your app must handle revocations by the sign-in service gracefully by sending the user to an interactive sign-in prompt to sign in again. For your reference: https://learn.microsoft.com/en-us/entra/identity-platform/refresh-tokens#token-expiration
Refer: Troubleshooting: Azure Site-to-Site VPN disconnects intermittently
Hope this helps and let me know if you need more assistance!
If the above is unclear or you are unsure about something, please add a comment below.
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