Azure VPN: a connection attempt failed because the connected party did not properly responded after a period of time, or established connection failed because connected host has failed to respond.

Question

Azure VPN: a connection attempt failed because the connected party did not properly responded after a period of time, or established connection failed because connected host has failed to respond.

Alexander S 0

I got a P2S VPN setup and using a OpenVPN(SSL) tunnel type.

My SKU is VPNGW1.

I got this error " a connection attempt failed because the connected party did not properly

responded after a period of time, or established connection failed because connected

host has failed to respond." right after verifying from the authenticator. I have not seen this error to the other machines though.

May I know your insights on this issue. TIA!

David Lapkovsky 0 Reputation points

2024-07-02T01:20:56.3533333+00:00

Hi Alexander, is your MFA setup and working? Are you getting any authentication requests in Microsoft Authenticator? Does your VPN use tokens or grid codes, or do you need to download your certificate manually? Is it working for anyone else?
Alexander S 0 Reputation points

2024-07-02T01:26:23.8866667+00:00

Hello David, yes MFA is working just fine. User was able to received authentication prompts in the ms authenticator app in phone. VPN uses config file downloaded from Azure and be imported in the Azure VPN Client installed in user device.

Tried the installation to other user and works perfectly fine.
Alexander S 0 Reputation points

2024-07-02T01:30:45.6333333+00:00

Not sure what triggers the issue.
David Lapkovsky 0 Reputation points

2024-07-02T02:32:23.1466667+00:00

Make sure all the windows updates are installed, including optional. Also turn on Receive updates for other Microsoft products under Windows Update —> Advanced Options

Also open a cmd prompt with admin rights, and perform the following commands in this sequence:

sfc /scannow

dism /online /cleanup-image /restorehealth

chkdsk c: /f /r (Choose Y, and hit enter when prompted)

While the first command is running, run Disk Cleanup as Administrator, check all boxes, hit Ok, and then Delete

Once all of the above is done, reboot, check for more updates and install them, and possibly repeat the steps above if the VPN still isn’t working.

Regards

2 answers

Your answer

David Lapkovsky 0 Reputation points

2024-07-02T01:20:56.3533333+00:00

Hi Alexander, is your MFA setup and working? Are you getting any authentication requests in Microsoft Authenticator? Does your VPN use tokens or grid codes, or do you need to download your certificate manually? Is it working for anyone else?
Alexander S 0 Reputation points

2024-07-02T01:26:23.8866667+00:00

Hello David, yes MFA is working just fine. User was able to received authentication prompts in the ms authenticator app in phone. VPN uses config file downloaded from Azure and be imported in the Azure VPN Client installed in user device.

Tried the installation to other user and works perfectly fine.
Alexander S 0 Reputation points

2024-07-02T01:30:45.6333333+00:00

Not sure what triggers the issue.
David Lapkovsky 0 Reputation points

2024-07-02T02:32:23.1466667+00:00

Make sure all the windows updates are installed, including optional. Also turn on Receive updates for other Microsoft products under Windows Update —> Advanced Options

Also open a cmd prompt with admin rights, and perform the following commands in this sequence:

sfc /scannow

dism /online /cleanup-image /restorehealth

chkdsk c: /f /r (Choose Y, and hit enter when prompted)

While the first command is running, run Disk Cleanup as Administrator, check all boxes, hit Ok, and then Delete

Once all of the above is done, reboot, check for more updates and install them, and possibly repeat the steps above if the VPN still isn’t working.

Regards

Answer 1

Sumit Singh 0

Hi

I have same issue Azure VPN use work and now stopped working

same VPN works on others machine

User's image

Sumit Singh 0 Reputation points

2026-02-20T14:39:05.2166667+00:00

@KapilAnanth Can you please suggest any solution

Answer 2

KapilAnanth 49,876 Moderator

@Alexander S ,

Welcome to the Microsoft Q&A Platform. Thank you for reaching out & I hope you are doing well.

I take it that you are using OpenVPN with Entra Authentication.

May I ask where exactly did you see this error?
Are you using Azure VPN Client and seeing this error in the "Failure reason"
- If so, can you please share a screenshot of the issue?
If you sign in with a different account, does the error persist?
If you use the same account in a different device, does the error persist?

Cheers,

Kapil

Alexander S 0 Reputation points

2024-07-02T00:46:25.2866667+00:00
@KapilAnanth ,

Yes, I'm using OpenVPN with Entra Authentication.

May I ask where exactly did you see this error?

Error is observed right after the login/authentication step. VPN wouldn't proceed and this error is displayed

Are you using Azure VPN Client and seeing this error in the "Failure reason"

If so, can you please share a screenshot of the issue?

If you sign in with a different account, does the error persist?

Yes, in their organization perhaps

If you use the same account in a different device, does the error persist

Can't verify since the user is using a company issued device and strict policy is implemented.
KapilAnanth 49,876 Reputation points Moderator

2024-07-02T06:48:03.29+00:00
@Alexander S ,

As next steps, you can try

#1 Reset VPN Gateway:

As the VPN was working initially, resetting an Azure VPN gateway or gateway connection is helpful if you lose cross-premises VPN connectivity on the VPN tunnels. You can follow the documentation here for implementation.

#2

Explore Command (Windows Key + E)

Right Click on "This PC", and select "Manage"

Once Computer Management Opens, click "Device Manager"

Under Network Adapters, uninstall all adapters starting with "WAN Miniport" - Right-click, Uninstall

Once you've uninstalled all, go to the menu and select "Scan for Hardware Changes" and those adapters will reinstall automatically without restarting.

Post this, try connecting to the VPN from the affected machine.

#3

If above does not help, you can enable Azure VPN Diagnostic Logs to help pinpoint the exact issue. You can take a look at P2SDiagnosticLog which can help you determine the cause of the issue.

Cheers,

Kapil
Alexander S 0 Reputation points

2024-07-03T00:37:50.4633333+00:00

This has been fixed. The root of this issue is a policy in Intune, it blocks the app from connecting to Azure server. We've added the application so that it will be exempted of that policy.

Appreciate the help. Thanks
KapilAnanth 49,876 Reputation points Moderator

2024-07-04T13:56:24.5033333+00:00

@Alexander S ,

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 have summarized our discussion and posted it as a new answer.

I would highly appreciate if you could "Accept" the answer and close this thread

Original posters help the community find answers faster by identifying the correct answer.

Thanks,

Kapil