Azure VPN connection dropping and reconnecting

Question

Azure VPN connection dropping and reconnecting

James Sefton 20

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

Ganesh Patapati 6,915 Reputation points Microsoft External Staff Moderator

2025-06-18T17:52:22.9966667+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. or Your 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-15

The 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.
James Sefton 20 Reputation points

2025-06-19T07:28:57.7033333+00:00

Hi Ganesh,

Thank you for your response. I have seen this issue before and so always ensure they are fully signed in to the application. Due to our organisational policies when they are disconnected it does require users to sign back in using their registered 365 account to our domain.

I think potentially it may be attempting to point to the Cisco VPN that we have installed (this was to facilitate our old phone system) I have gone ahead and uninstalled this to see if that has any impact.

If it was an Entra issue with expired tokens, would it not be affecting all of our staff? We have 65-70 staff on our second floor who all connect to the same VPN connection.

Thank you,

James
Ganesh Patapati 6,915 Reputation points Microsoft External Staff Moderator

2025-06-19T10:00:45.9666667+00:00
Hello James Sefton

Could you kindly provide the following details:

Are there any error messages on the VPN client when it disconnects? If yes, please share the error Screenshot of the VPN disconnections.

Can you please confirm which authentication or tunnel protocol type are using on azure VPN?

Can you be able to check Entra sign-in logs for affected users to see if token renewal is failing silently?

Do you see any ping drops during these disconnections?

Meantime,

Refer this article: https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-troubleshoot-vpn-point-to-site-connection-problems#reauthenticate

Hope this helps and let me know if you need more assistance!
Ganesh Patapati 6,915 Reputation points Microsoft External Staff Moderator

2025-06-20T17:41:55.36+00:00

Hello James Sefton

Could you please share the necessary details for further troubleshooting the issue? If you have any updates on this issue, feel free to post back.
Ganesh Patapati 6,915 Reputation points Microsoft External Staff Moderator

2025-06-23T08:33:41.7533333+00:00

Hello James Sefton

Could you please share the necessary details for further troubleshooting the issue? If you have any updates on this issue, feel free to post back.
James Sefton 20 Reputation points

2025-06-23T08:38:00.4566667+00:00

Hi Ganesh,

It seems uninstalling the other VPN has remediated this issue.

I have caught up with 2 users experiencing the issue and have noted that their VPN has not cut out.

Thanks,

James

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James Sefton 20 Reputation points

2025-06-19T07:28:57.7033333+00:00

Hi Ganesh,

Thank you for your response. I have seen this issue before and so always ensure they are fully signed in to the application. Due to our organisational policies when they are disconnected it does require users to sign back in using their registered 365 account to our domain.

I think potentially it may be attempting to point to the Cisco VPN that we have installed (this was to facilitate our old phone system) I have gone ahead and uninstalled this to see if that has any impact.

If it was an Entra issue with expired tokens, would it not be affecting all of our staff? We have 65-70 staff on our second floor who all connect to the same VPN connection.

Thank you,

James
Ganesh Patapati 6,915 Reputation points Microsoft External Staff Moderator

2025-06-19T10:00:45.9666667+00:00

Hello James Sefton

Could you kindly provide the following details:

Are there any error messages on the VPN client when it disconnects? If yes, please share the error Screenshot of the VPN disconnections.

Can you please confirm which authentication or tunnel protocol type are using on azure VPN?

Can you be able to check Entra sign-in logs for affected users to see if token renewal is failing silently?

Do you see any ping drops during these disconnections?

Meantime,

Refer this article: https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-troubleshoot-vpn-point-to-site-connection-problems#reauthenticate

Hope this helps and let me know if you need more assistance!
Ganesh Patapati 6,915 Reputation points Microsoft External Staff Moderator

2025-06-20T17:41:55.36+00:00

Hello James Sefton

Could you please share the necessary details for further troubleshooting the issue? If you have any updates on this issue, feel free to post back.
Ganesh Patapati 6,915 Reputation points Microsoft External Staff Moderator

2025-06-23T08:33:41.7533333+00:00

Hello James Sefton

Could you please share the necessary details for further troubleshooting the issue? If you have any updates on this issue, feel free to post back.
James Sefton 20 Reputation points

2025-06-23T08:38:00.4566667+00:00

Hi Ganesh,

It seems uninstalling the other VPN has remediated this issue.

I have caught up with 2 users experiencing the issue and have noted that their VPN has not cut out.

Thanks,

James

Answer 1

Ganesh Patapati 6,915 Microsoft External Staff Moderator

Hello @James Sefton

I'm glad that you were able to resolve your issue and thank you for posting your solution so that others experiencing the same thing can easily reference this!

Since the Microsoft Q&A community has a policy that "The question author cannot accept their own answer. They can only accept answers by others", I'll repost your solution.

Please click "Accept" the answer as original posters help the community find answers faster by identifying the correct answer.

Issue: Azure VPN connection dropping and reconnecting

Resolution: It seems uninstalling the other VPN has remediated this issue.

I have caught up with 2 users experiencing the issue and have noted that their VPN has not cut out.

Please don’t forget to close the thread by clicking "Accept the answer" and “Up-vote" wherever the information provided helps you, as this can be beneficial to other community members. Accepted answer

Ganesh Patapati 6,915 Reputation points Microsoft External Staff Moderator

2025-06-23T09:15:57.9966667+00:00

Hello @James Sefton

Thanks for the response!

Since the Microsoft Q&A community has a policy that "The question author cannot accept their own answer. They can only accept answers by others", I'll repost your solution.

Please don’t forget to close the thread by clicking "Accept the answer" and “Up-vote" wherever the information provided helps you, as this can be beneficial to other community members.

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Azure VPN connection dropping and reconnecting

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