Azure VPN Client on macOS 13 connects but cannot access resources

Question

Azure VPN Client on macOS 13 connects but cannot access resources

Paul Knisely 0

Azure VPN Client is installed through the Mac App Store and is able to connect but cannot ping devices. When Azure VPN Client is installed in a Parallels Windows 11 VM, it connects and is able to ping devices through the VPN.

Testing through Windows 11 is fine and everything but my development tools are all Mac based.

Bianca Malan 0 Reputation points

2023-10-23T20:46:06.0233333+00:00

Could you share some screenshots of the current network settings?
Paul Knisely 0 Reputation points

2023-10-23T21:05:58.32+00:00

Certainly. What specific network settings would you like to see?
Paul Knisely 0 Reputation points

2023-10-23T22:05:11.0666667+00:00

To add more context to what I have done.

I have installed Rosetta 2 (I'm on an M1 mac) without success.
I have also manually updated the service order through the cli to make sure the Azure VPN service is at the top of the list. The mac GUI doesn't show VPN clients so this has to be configured using the 'networksetup' command.
ChaitanyaNaykodi-MSFT 27,476 Reputation points Microsoft Employee Moderator

2023-10-24T03:59:38.4133333+00:00

@Paul Knisely

Thank you for reaching out.

Based on your statement above.

I have installed Rosetta 2 (I'm on an M1 mac) without success.

Not exactly sure if it is a typo or you were not able to install Rosetta 2 successfully. As Rosetta doesn’t come pre-installed on Apple Silicon M1 or M2 Macs. This means you will have to download and install it on your own.
If Rosetta is not installed on the machine the mactunnelextension plugin was not able to launch.

This is currently discussed in this thread here.

If above is a typo and you have installed Rosetta 2 successfully then it can help troubleshoot if you can take a look at the application logs. Application logs can be found from Settings -> Show Logs Directory OR

Under folder: /Users/<CurrentUser>/Library/GroupContainers/UBF8T346G9.group.com.microsoft.AzureVpnMac.shared/LogFiles

Application control plane logs file is named AzureVpnClient.log. Application data plane OpenVPN protocol level logs file com.microsoft.AzureVpnMac.PacketTunnel*.log .

Please let us know if you are able to locate any errors in the logs. Thank you!
Paul Knisely 0 Reputation points

2023-10-24T12:43:50.16+00:00

My apologies for the confusing statement. I have successfully installed Rosetta 2 on my M1 Mac. I also see the mactunnelextension plugin appear in Activity Monitor when Azure VPN Client is running and connected.

Installing Rosetta 2 and making sure Azure VPN Client is using Rosetta 2, has not solved my issue with the VPN client not working. That thread you linked is the one I used in an attempt to find a solution.

I do see that log file and content gets appended to that file. No errors in that log file appear to me but I'm also not entirely sure what type of errors I'm looking for.
ChaitanyaNaykodi-MSFT 27,476 Reputation points Microsoft Employee Moderator

2023-10-27T20:43:05.6+00:00

@Paul Knisely

Just following up here to see if you were able take a look at my comment above. Thank you!
Paul Knisely 0 Reputation points

2023-10-30T12:03:42.09+00:00

@ChaitanyaNaykodi-MSFT still looking into it and using your suggestions.
ChaitanyaNaykodi-MSFT 27,476 Reputation points Microsoft Employee Moderator

2023-11-01T03:09:39.5733333+00:00

@Paul Knisely

Sounds good, please let me know if the issue still persists. Thank you!

1 answer

Your answer

Bianca Malan 0 Reputation points

2023-10-23T20:46:06.0233333+00:00

Could you share some screenshots of the current network settings?
Paul Knisely 0 Reputation points

2023-10-23T21:05:58.32+00:00

Certainly. What specific network settings would you like to see?
Paul Knisely 0 Reputation points

2023-10-23T22:05:11.0666667+00:00

To add more context to what I have done.

I have installed Rosetta 2 (I'm on an M1 mac) without success.
I have also manually updated the service order through the cli to make sure the Azure VPN service is at the top of the list. The mac GUI doesn't show VPN clients so this has to be configured using the 'networksetup' command.
ChaitanyaNaykodi-MSFT 27,476 Reputation points Microsoft Employee Moderator

2023-10-24T03:59:38.4133333+00:00

@Paul Knisely

Thank you for reaching out.

Based on your statement above.

I have installed Rosetta 2 (I'm on an M1 mac) without success.

Not exactly sure if it is a typo or you were not able to install Rosetta 2 successfully. As Rosetta doesn’t come pre-installed on Apple Silicon M1 or M2 Macs. This means you will have to download and install it on your own.
If Rosetta is not installed on the machine the mactunnelextension plugin was not able to launch.

This is currently discussed in this thread here.

If above is a typo and you have installed Rosetta 2 successfully then it can help troubleshoot if you can take a look at the application logs. Application logs can be found from Settings -> Show Logs Directory OR

Under folder: /Users/<CurrentUser>/Library/GroupContainers/UBF8T346G9.group.com.microsoft.AzureVpnMac.shared/LogFiles

Application control plane logs file is named AzureVpnClient.log. Application data plane OpenVPN protocol level logs file com.microsoft.AzureVpnMac.PacketTunnel*.log .

Please let us know if you are able to locate any errors in the logs. Thank you!
Paul Knisely 0 Reputation points

2023-10-24T12:43:50.16+00:00

My apologies for the confusing statement. I have successfully installed Rosetta 2 on my M1 Mac. I also see the mactunnelextension plugin appear in Activity Monitor when Azure VPN Client is running and connected.

Installing Rosetta 2 and making sure Azure VPN Client is using Rosetta 2, has not solved my issue with the VPN client not working. That thread you linked is the one I used in an attempt to find a solution.

I do see that log file and content gets appended to that file. No errors in that log file appear to me but I'm also not entirely sure what type of errors I'm looking for.
ChaitanyaNaykodi-MSFT 27,476 Reputation points Microsoft Employee Moderator

2023-10-27T20:43:05.6+00:00

@Paul Knisely

Just following up here to see if you were able take a look at my comment above. Thank you!
Paul Knisely 0 Reputation points

2023-10-30T12:03:42.09+00:00

@ChaitanyaNaykodi-MSFT still looking into it and using your suggestions.
ChaitanyaNaykodi-MSFT 27,476 Reputation points Microsoft Employee Moderator

2023-11-01T03:09:39.5733333+00:00

@Paul Knisely

Sounds good, please let me know if the issue still persists. Thank you!

Answer 1

@Paul Knisely

Thank you for getting back and sharing additional details.

As no error is observed and the connection successfully established. This might be a routing issue. You can try the following steps and see if that helps in troubleshooting the issue.

Run the ifconfig command in your Mac's terminal and check the interface name and IP address of the VpnCLient.
You can also find the allocated IpAddress & total connection connected time from Network Preferences:
Route table: - This will help debugging if correct routes are configured for VpnClient connected interface You can look at route table using netstat -rn command on Terminal
Make sure the configured routes have that endpoint/IpAddress for which connectivity is not working. If it does not have, then the issue is the missing route.
Make sure ICMP traffic is not blocked on the MAC and you can do TCP ping instead to check the connectivity.
If the routes are correct you can try to redownload VPN client profile from Server & import it to client again.

Hope this helps! Please let me know if you have any additional questions. Thank you!

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Azure VPN Client on macOS 13 connects but cannot access resources

1 answer

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