Azure VPN Client not working on MAC book 2023 M2

Air2 35

When I connect the VPN it stays disconnected, but the log says:

05/11/2023 11:49:09: Information Dialing VPN connection XXXX Azure VPN, Status = Success

05/11/2023 11:49:09: Information Dialing VPN connection XXXX Azure VPN

05/11/2023 11:49:09: Information Saving AAD User Account

05/11/2023 11:49:09: Information Successfully Received AAD Credential Token. User: xxx@xxxx.com

05/11/2023 11:48:36: Information The VPN connection profile XXXX Azure VPN is added/imported successfully.

05/11/2023 11:48:36: Information Application Initialized

I use the same configuration on my old mid 2015 MacBook, on this old MacBook it works fine. A colleague uses a 2019 MacBook (intel) and it works also fine. But on my brand new m2 MacBook it does not work. My colleague and I use the same version of Ventura: 13.3.1 (a)

How can I get more info on what is going wrong here?

Sumaia Ratib Ali Awadallah 15 Reputation points

2023-05-11T10:07:43.4466667+00:00

I have the same question
Sumaia Ratib Ali Awadallah 15 Reputation points

2023-05-11T10:08:05.2733333+00:00

I have the same question
ChaitanyaNaykodi-MSFT 22,776 Reputation points Microsoft Employee

2023-05-11T20:58:14.15+00:00

@Air2 & @Sumaia Ratib Ali Awadallah

Thank you for reaching out on the Microsoft Q&A forum.

If I understand correctly, you are facing an issue with the Azure VPN Client on your MAC book 2023 M2. Based on the logs shared above there appears to be no error but still the VPN connection stays disconnected.

You can try running additional troubleshooting steps mentioned below and see if that helps in pin-pointing the issue.

As there is no error observed on the VPN Client's UI, 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 by in the logs. Thank you!

Air2 35

The AzureVpnClient.log contains the following, it is also the only file in that log files directory:

This is Log file.05/12/2023 08:04:16 Information Application Initialized
05/12/2023 08:04:16 Information importBackedUpVpnConnectionsProfiles: List of all backed up Vpn connection profiles' xml files: [file:///Users/xxxx/Library/Containers/com.microsoft.AzureVpnMac/Data/Library/Application%20Support/com.microsoft.AzureVpnMac/XXXXX%20Azure%20VPN.AzureVpnProfile.xml]
05/12/2023 08:04:16 Information importBackedUpVpnConnectionsProfiles: List of all backed up Vpn connection profiles' xml files' urls: [file:///Users/xxxx/Library/Containers/com.microsoft.AzureVpnMac/Data/Library/Application%20Support/com.microsoft.AzureVpnMac/XXXXX%20Azure%20VPN.AzureVpnProfile.xml]
05/12/2023 08:04:16 Information Decoded profile. Group token flag status false version 1
05/12/2023 08:04:16 Information profileXmlToObject: Imported AzVpnProfile: XXXXX Azure VPN object
05/12/2023 08:04:16 Information importBackedUpVpnConnectionsProfiles: Backed up VpnConnection profile: XXXXX Azure VPN getting imported from XML file: file:///Users/xxxx/Library/Containers/com.microsoft.AzureVpnMac/Data/Library/Application%20Support/com.microsoft.AzureVpnMac/XXXXX%20Azure%20VPN.AzureVpnProfile.xml is valid.
05/12/2023 08:04:16 Information The VPN connection profile XXXXX Azure VPN is added/imported successfully.
05/12/2023 08:04:16 Information Removing stale vpn managers
05/12/2023 08:04:20 Information Group token flag status: false
05/12/2023 08:04:20 Information getClientAuthLoginCredentials: Using account: com.microsoft.AzureVpnMac
05/12/2023 08:04:20 
05/12/2023 08:04:20 
05/12/2023 08:04:20 Information sAcquireTokenInteractivelyNeeded: Account is not saved so interactive login will be needed.
05/12/2023 08:04:20 
05/12/2023 08:04:20 Information removeClientAuthLoginCredentials: Using account: com.microsoft.AzureVpnMac
05/12/2023 08:04:20 Information getClientAuthLoginCredentials: Using account: com.microsoft.AzureVpnMac
05/12/2023 08:04:20 
05/12/2023 08:04:20 Warning removeClientAuthLoginCredentials: Failed to retrive previously saved ClientAuth: aad secret for Vpn connection: XXXXX Azure VPN, so no cleanup is needed!
05/12/2023 08:04:20 Information IsAcquireTokenInteractivelyNeeded: Cleared saved AAD auth login account Username from KeyChain as user will need to do interactive login to acquire AAD token.
05/12/2023 08:04:20 Information Acquiring AAD token interactively...
05/12/2023 08:05:55 Information Successfully Received AAD Credential Token. User: xxx@XXXXX.com
05/12/2023 08:05:55 Information Saving AAD User Account
05/12/2023 08:05:55 Information Dialing VPN connection XXXXX Azure VPN
05/12/2023 08:05:55 Information Dialing VPN connection XXXXX Azure VPN, Status = Success

I cannot find any com.microsoft.AzureVpnMac.PacketTunnel*.log files I can find this directory:

/Users/xxxx/Library/Containers/com.microsoft.AzureVpnMac.PacketTunnel/Data/Library/Application Scripts/com.microsoft.AzureVpnMac.PacketTunnel

However it is empty.

Edit:

On an other Mac I see the com.microsoft.AzureVpnMac.PacketTunnel*.log should be in the same directory as the AzureVpnClient.log, on my new MacBook it is not. So something is going wrong, but I cannot see what it is.

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Accepted answer

ChaitanyaNaykodi-MSFT 22,776 Reputation points Microsoft Employee

2023-05-24T14:57:00.5+00:00

@Air2 & @David Pulley & @Sumaia Ratib Ali Awadallah

We got an update regarding this issue from the product team.

Installing Rosetta app helped in resolving the issue.

The root cause for this issue is:

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.
As Rosetta was not installed on the machine the mactunnelextension plugin was not able to launch.

What is Rosetta?
Rosetta 2 enables a Mac with Apple silicon to use apps built for a Mac with an Intel processor.
More details can be found here: If you need to install Rosetta on your Mac - Apple Support

We understand this is currently not documented; we will work with the team to get this added to our documentation.

@Air2 if I understand correctly, for you the issue was resolved after installing the Rosetta App.

Please let us know if you have any further questions. Thank you!

It will be helpful if you can "Accept the answer" if the information helped you. This will help us and others in the community as well.
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3 additional answers

Air2 35 Reputation points

2023-05-24T17:34:04.0766667+00:00

For me it solved the issue. To manual install rosetta2 you need to run a commandline prompt because the azure vpn client does not request it, which it normally should. So i consider this a work around and I really suggest to update the azure vpn client to make it request this software as it should
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2 people found this answer helpful.

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ChaitanyaNaykodi-MSFT 22,776 Microsoft Employee

@Air2

Thank you for getting back and sharing additional details.

On an other Mac I see the com.microsoft.AzureVpnMac.PacketTunnel*.log should be in the same directory as the AzureVpnClient.log, on my new MacBook it is not. So something is going wrong, but I cannot see what it is.

Your understanding here is correct. As the protocol level com.microsoft.AzureVpnMac.PacketTunnel*.log file is missing the likely issue is that mactunnelextension process is not able to start. You can confirm this by trying to connect from client & and open Activity Monitor to check if mactunnelextension process is running or not. You can also check for logs in the Console App and apply a filter for networkextension and see if you are able to observe any errors.

Ref: https://support.apple.com/guide/console/log-messages-cnsl1012/mac

If you are unable to observe any errors the appropriate action here will be to create a support request as a support engineer can take a deeper look at the logs and provide additional insights specific to your environment. If you have a support plan you may file a support ticket, else could you please send an email to azcommunity@microsoft.com with the below details. I will help create a one-time free support ticket for you in this case.

Subject : Attn Chaitanya

Thread URL: Link to this thread.

Subscription ID

Please let me know once you have done the same.

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

Air2 35

@ChaitanyaNaykodi-MSFT

The mactunnelprocess was not running and in the console log there are indeed errors of it not starting. I supplied the log below (see line 63, 65, 66 I will paste them again below the full log

default	09:12:40.156984+0200	nsurlsessiond	UUID cache generation changed from 482 to 483
default	09:12:40.157552+0200	nsurlsessiond	UUID cache miss for com.apple.geod
default	09:12:40.162733+0200	neagent	Failed to find com.apple.geod in LaunchServices
default	09:12:40.164736+0200	nehelper	Failed to find com.apple.geod using neagent
default	09:12:40.165256+0200	nehelper	UUID cache generation changed from 482 to 483
default	09:12:40.168437+0200	nehelper	Setting UUID cache generation to 484
default	09:13:40.433734+0200	Azure VPN Client	Current bundle (/Applications/Azure VPN Client.app) does not have a SystemExtensions directory
default	09:13:40.434940+0200	Azure VPN Client	 Saving configuration XXXXX Azure VPN with existing signature {length = 20, bytes = 0x9b704fbbd9a952d3a11cb5c9674b7c9198f526b2}
default	09:13:40.453269+0200	nehelper	Adding F66E57F9-AF3D-4A5E-8154-4E5519BE4672 to the loaded configurations
default	09:13:40.453403+0200	Azure VPN Client	Received a com.apple.neconfigurationchanged notification with token 31
default	09:13:40.453356+0200	nehelper	Successfully posted generation 47
default	09:13:40.453608+0200	Azure VPN Client	 Successfully saved configuration XXXXX Azure VPN
default	09:13:40.453583+0200	nehelper	Received a com.apple.neconfigurationchanged notification with token 12
default	09:13:40.453876+0200	Azure VPN Client	Sending load command to nehelper
default	09:13:40.453910+0200	Azure VPN Client	Clearing F66E57F9-AF3D-4A5E-8154-4E5519BE4672 from the loaded configurations
default	09:13:40.454395+0200	Azure VPN Client	Adding F66E57F9-AF3D-4A5E-8154-4E5519BE4672 to the loaded configurations
default	09:13:40.453690+0200	nesessionmanager	Received a com.apple.neconfigurationchanged notification with token 23
default	09:13:40.454652+0200	nesessionmanager	Clearing F66E57F9-AF3D-4A5E-8154-4E5519BE4672 from the loaded configurations
default	09:13:40.454819+0200	nesessionmanager	Adding F66E57F9-AF3D-4A5E-8154-4E5519BE4672 to the loaded configurations
default	09:13:40.455106+0200	UserEventAgent	Received notification com.apple.neconfigurationchanged
default	09:13:40.454842+0200	nesessionmanager	Reload from disk complete
default	09:13:40.455034+0200	nesessionmanager	Got a configuration change callback with configuration IDs (
    "F66E57F9-AF3D-4A5E-8154-4E5519BE4672"
)
default	09:13:40.455534+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Resetting VPN On Demand
default	09:13:40.455656+0200	nesessionmanager	Found 0 (0 active) registrations for com.microsoft.AzureVpnMac.PacketTunnel (com.apple.networkextension.packet-tunnel)
default	09:13:40.455735+0200	nesessionmanager	Found 0 (0 active) registrations for com.microsoft.AzureVpnMac.PacketTunnel (com.apple.networkextension.packet-tunnel)
default	09:13:40.455970+0200	nesessionmanager	com.microsoft.AzureVpnMac[inactive]: starting
default	09:13:40.456003+0200	UserEventAgent	Not generating a configuration changed event because no configurations are present that need active sessions
default	09:13:40.456248+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)] in state NESMVPNSessionStateIdle: update configuration
default	09:13:40.473479+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Received a start command from Azure VPN Client[3332]
default	09:13:40.473509+0200	nesessionmanager	Registering session NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]
default	09:13:40.473671+0200	nesessionmanager	<NESMServer: 0x141707890>: Register Enterprise VPN Session: NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]
default	09:13:40.473697+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Successfully registered
default	09:13:40.474536+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: status changed to connecting
default	09:13:40.474775+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)] in state NESMVPNSessionStateIdle: received start message
default	09:13:40.474803+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Leaving state NESMVPNSessionStateIdle
default	09:13:40.474822+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Entering state NESMVPNSessionStatePreparingNetwork
default	09:13:40.475184+0200	nesessionmanager	Found 0 (0 active) registrations for com.microsoft.AzureVpnMac.PacketTunnel (com.apple.networkextension.packet-tunnel)
default	09:13:40.475419+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Leaving state NESMVPNSessionStatePreparingNetwork
default	09:13:40.478610+0200	neagent	Looking for an extension with identifier com.microsoft.AzureVpnMac.PacketTunnel and extension point com.apple.networkextension.packet-tunnel
default	09:13:40.480449+0200	neagent	[d <private>] <PKHost:0x13ff0c400> Beginning discovery for flags: 0, point: com.apple.networkextension.packet-tunnel
default	09:13:40.475452+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Entering state NESMVPNSessionStateStarting
default	09:13:40.475531+0200	nesessionmanager	NEVPNTunnelPlugin(com.microsoft.AzureVpnMac[inactive]): Sending start command
default	09:13:40.475605+0200	nesessionmanager	com.microsoft.AzureVpnMac[inactive]: starting
default	09:13:40.486265+0200	neagent	Looking for an extension with identifier com.microsoft.AzureVpnMac.PacketTunnel and extension point com.apple.networkextension.packet-tunnel
default	09:13:40.486438+0200	neagent	[d <private>] <PKHost:0x13ff0c400> Beginning discovery for flags: 0, point: com.apple.networkextension.packet-tunnel
default	09:13:40.490653+0200	neagent	Found 1 extension(s) with identifier com.microsoft.AzureVpnMac.PacketTunnel and extension point com.apple.networkextension.packet-tunnel
default	09:13:40.491070+0200	neagent	Found 1 extension(s) with identifier com.microsoft.AzureVpnMac.PacketTunnel and extension point com.apple.networkextension.packet-tunnel
default	09:13:40.490926+0200	nesessionmanager	com.microsoft.AzureVpnMac[562]: disposing
default	09:13:40.491502+0200	neagent	Beginning extension request with extension com.microsoft.AzureVpnMac.PacketTunnel
default	09:13:40.491292+0200	nesessionmanager	com.microsoft.AzureVpnMac[562]: Tearing down agent connection
default	09:13:40.491328+0200	nesessionmanager	com.microsoft.AzureVpnMac[562]: XPC connection went away
default	09:13:40.491394+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Plugin is installed
default	09:13:40.493706+0200	UserEventAgent	Current file handles for com.apple.networkextension.file-descriptor-maintainer: (
    "Policy Session VPN control socket (47)",
    "Policy Session VPN high socket (50)",
    "Policy Session MasterSession socket (51)",
    "Policy Session LowPrioritySession socket (52)",
    "Network Agent Registration socket (53) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0"
)
default	09:13:40.501899+0200	UserEventAgent	File Handle Maintainer listening for readable events on Network Agent Registration socket (53) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0
error	09:13:40.513319+0200	nesessionmanager	Validation failed - no audit tokens
error	09:13:40.513351+0200	nesessionmanager	NEVPNTunnelPlugin(com.microsoft.AzureVpnMac[inactive]): Validation of the extension failed
default	09:13:40.512908+0200	neagent	Extension request with extension com.microsoft.AzureVpnMac.PacketTunnel started with identifier (null)
error	09:13:40.513154+0200	neagent	Failed to start extension com.microsoft.AzureVpnMac.PacketTunnel: Error Domain=PlugInKit Code=4 "RBSLaunchRequest error trying to launch plugin com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211): Error Domain=RBSRequestErrorDomain Code=5 "Launch failed." UserInfo={NSLocalizedFailureReason=Launch failed., NSUnderlyingError=0x15b324870 {Error Domain=NSPOSIXErrorDomain Code=111 "Unknown error: 111" UserInfo={NSLocalizedDescription=Launchd job spawn failed}}}" UserInfo={NSLocalizedDescription=RBSLaunchRequest error trying to launch plugin com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211): Error Domain=RBSRequestErrorDomain Code=5 "Launch failed." UserInfo={NSLocalizedFailureReason=Launch failed., NSUnderlyingError=0x15b324870 {Error Domain=NSPOSIXErrorDomain Code=111 "Unknown error: 111" UserInfo={NSLocalizedDescription=Launchd job spawn failed}}}}
default	09:13:40.514158+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)] in state NESMVPNSessionStateStarting: plugin NEVPNTunnelPlugin(com.microsoft.AzureVpnMac[inactive]) started with PID 0 error (null)
default	09:13:40.514823+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Leaving state NESMVPNSessionStateStarting
default	09:13:40.514851+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Entering state NESMVPNSessionStateStopping, timeout 20 seconds
default	09:13:40.514887+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: config request: pushing handler [(null)] (null)
default	09:13:40.514908+0200	nesessionmanager	<NESMServer: 0x141707890>: Request to uninstall session: NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]
default	09:13:40.514925+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: status changed to disconnecting
default	09:13:40.514951+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Updated network agent (inactive, compulsory, not-user-activiated, not-kernel-activated)
default	09:13:40.515103+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)] in state NESMVPNSessionStateStopping: session is now uninstalled
default	09:13:40.515126+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)] in state NESMVPNSessionStateStopping: plugin already disconnected, disposing all plugins
default	09:13:40.515146+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Leaving state NESMVPNSessionStateStopping
default	09:13:40.515166+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Entering state NESMVPNSessionStateDisposing, timeout 5 seconds
default	09:13:40.515192+0200	nesessionmanager	com.microsoft.AzureVpnMac[562]: disposing
default	09:13:40.515396+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: config request: popping handler [(null)] (null)
default	09:13:40.515393+0200	nesessionmanager	com.microsoft.AzureVpnMac[562]: Tearing down agent connection
default	09:13:40.515484+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)] in state NESMVPNSessionStateDisposing: plugin NEVPNTunnelPlugin(com.microsoft.AzureVpnMac[inactive]) dispose complete
default	09:13:40.515583+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)] in state NESMVPNSessionStateDisposing: all plugins have disposed
default	09:13:40.515880+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Leaving state NESMVPNSessionStateDisposing
default	09:13:40.515922+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: Entering state NESMVPNSessionStateIdle
default	09:13:40.515467+0200	nesessionmanager	com.microsoft.AzureVpnMac[562]: XPC connection went away
default	09:13:40.516185+0200	nesessionmanager	NESMVPNSession[Primary Tunnel:XXXXX Azure VPN:F66E57F9-AF3D-4A5E-8154-4E5519BE4672:(null)]: status changed to disconnected, last stop reason Plugin failed
default	09:13:40.515516+0200	nesessionmanager	NEVPNTunnelPlugin(com.microsoft.AzureVpnMac[inactive]): Tearing down plugin connection
default	09:13:40.520056+0200	UserEventAgent	Current file handles for com.apple.networkextension.file-descriptor-maintainer: (
    "Policy Session VPN control socket (48)",
    "Policy Session VPN high socket (54)",
    "Policy Session MasterSession socket (55)",
    "Policy Session LowPrioritySession socket (56)",
    "Network Agent Registration socket (57) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0"
)
default	09:13:40.520345+0200	UserEventAgent	File Handle Maintainer listening for readable events on Network Agent Registration socket (57) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0
default	09:13:40.521537+0200	UserEventAgent	Current file handles for com.apple.networkextension.file-descriptor-maintainer: (
    "Policy Session VPN control socket (47)",
    "Policy Session VPN high socket (50)",
    "Policy Session MasterSession socket (51)",
    "Policy Session LowPrioritySession socket (52)",
    "Network Agent Registration socket (53) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0"
)
default	09:13:40.522295+0200	UserEventAgent	File Handle Maintainer listening for readable events on Network Agent Registration socket (53) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0
default	09:13:40.524772+0200	UserEventAgent	Current file handles for com.apple.networkextension.file-descriptor-maintainer: (
    "Policy Session VPN control socket (48)",
    "Policy Session VPN high socket (54)",
    "Policy Session MasterSession socket (55)",
    "Policy Session LowPrioritySession socket (56)",
    "Network Agent Registration socket (57) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0"
)
default	09:13:40.524992+0200	UserEventAgent	File Handle Maintainer listening for readable events on Network Agent Registration socket (57) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0
default	09:13:40.525794+0200	UserEventAgent	Current file handles for com.apple.networkextension.file-descriptor-maintainer: (
    "Policy Session VPN control socket (47)",
    "Policy Session VPN high socket (50)",
    "Policy Session MasterSession socket (51)",
    "Policy Session LowPrioritySession socket (52)",
    "Network Agent Registration socket (53) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0"
)
default	09:13:40.525933+0200	UserEventAgent	File Handle Maintainer listening for readable events on Network Agent Registration socket (53) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0
default	09:13:40.527137+0200	UserEventAgent	Current file handles for com.apple.networkextension.file-descriptor-maintainer: (
    "Policy Session VPN control socket (48)",
    "Policy Session VPN high socket (54)",
    "Policy Session MasterSession socket (55)",
    "Policy Session LowPrioritySession socket (56)",
    "Network Agent Registration socket (57) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0"
)
default	09:13:40.527293+0200	UserEventAgent	File Handle Maintainer listening for readable events on Network Agent Registration socket (57) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0
default	09:13:40.528729+0200	UserEventAgent	Current file handles for com.apple.networkextension.file-descriptor-maintainer: (
    "Policy Session VPN control socket (47)",
    "Policy Session VPN high socket (50)",
    "Policy Session MasterSession socket (51)",
    "Policy Session LowPrioritySession socket (52)",
    "Network Agent Registration socket (53) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0"
)
default	09:13:40.528829+0200	UserEventAgent	File Handle Maintainer listening for readable events on Network Agent Registration socket (53) F66E57F9-AF3D-4A5E-8154-4E5519BE4672 D1D16B5B-D7CC-413D-B710-D5E96F4B7D3B 1 (null) agent flags 0

The error messages:

error 09:13:40.513319+0200 nesessionmanager Validation failed - no audit tokens
error 09:13:40.513351+0200 nesessionmanager NEVPNTunnelPlugin(com.microsoft.AzureVpnMac[inactive]): Validation of the extension failed
default 09:13:40.512908+0200 neagent Extension request with extension com.microsoft.AzureVpnMac.PacketTunnel started with identifier (null)
error 09:13:40.513154+0200 neagent Failed to start extension com.microsoft.AzureVpnMac.PacketTunnel: Error Domain=PlugInKit Code=4 "RBSLaunchRequest error trying to launch plugin com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211): Error Domain=RBSRequestErrorDomain Code=5 "Launch failed." UserInfo={NSLocalizedFailureReason=Launch failed., NSUnderlyingError=0x15b324870 {Error Domain=NSPOSIXErrorDomain Code=111 "Unknown error: 111" UserInfo={NSLocalizedDescription=Launchd job spawn failed}}}" UserInfo={NSLocalizedDescription=RBSLaunchRequest error trying to launch plugin com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211): Error Domain=RBSRequestErrorDomain Code=5 "Launch failed." UserInfo={NSLocalizedFailureReason=Launch failed., NSUnderlyingError=0x15b324870 {Error Domain=NSPOSIXErrorDomain Code=111 "Unknown error: 111" UserInfo={NSLocalizedDescription=Launchd job spawn failed}}}}

Also this are there errors when filtering on neagent:

default 09:12:40.162733+0200 neagent Failed to find com.apple.geod in LaunchServices
default 09:12:40.164736+0200 nehelper Failed to find com.apple.geod using neagent
default 09:13:40.478610+0200 neagent Looking for an extension with identifier com.microsoft.AzureVpnMac.PacketTunnel and extension point com.apple.networkextension.packet-tunnel
default 09:13:40.480449+0200 neagent [d <private>] <PKHost:0x13ff0c400> Beginning discovery for flags: 0, point: com.apple.networkextension.packet-tunnel
default 09:13:40.486265+0200 neagent Looking for an extension with identifier com.microsoft.AzureVpnMac.PacketTunnel and extension point com.apple.networkextension.packet-tunnel
default 09:13:40.486438+0200 neagent [d <private>] <PKHost:0x13ff0c400> Beginning discovery for flags: 0, point: com.apple.networkextension.packet-tunnel
default 09:13:40.489670+0200 neagent [d <private>] <PKHost:0x13ff0c400> Completed discovery. Final # of matches: 1
default 09:13:40.490653+0200 neagent Found 1 extension(s) with identifier com.microsoft.AzureVpnMac.PacketTunnel and extension point com.apple.networkextension.packet-tunnel
default 09:13:40.490888+0200 neagent [d <private>] <PKHost:0x13ff0c400> Completed discovery. Final # of matches: 1
default 09:13:40.491070+0200 neagent Found 1 extension(s) with identifier com.microsoft.AzureVpnMac.PacketTunnel and extension point com.apple.networkextension.packet-tunnel
default 09:13:40.491502+0200 neagent Beginning extension request with extension com.microsoft.AzureVpnMac.PacketTunnel
default 09:13:40.492295+0200 neagent [u 767B26BD-D966-4021-8D56-322B7BFA4211:m (null)] [<private>(<private>)] Ready plugins sent as euid = 501, uid = 501, personaid = -1, type = NOPERSONA, name = <unknown>
default 09:13:40.498675+0200 runningboardd Launch request for xpcservice<com.microsoft.AzureVpnMac.PacketTunnel([osservice<com.apple.neagent(501)>:562:562])(501)> is using uid 501 (divined from auid 501 euid 501)
default 09:13:40.498733+0200 runningboardd Executing launch request for xpcservice<com.microsoft.AzureVpnMac.PacketTunnel([osservice<com.apple.neagent(501)>:562:562])(501)> (Launching extension com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211) for host 562)
default 09:13:40.498903+0200 runningboardd Creating and launching job for: xpcservice<com.microsoft.AzureVpnMac.PacketTunnel([osservice<com.apple.neagent(501)>:562:562])(501)>
error 09:13:40.512542+0200 neagent [u 767B26BD-D966-4021-8D56-322B7BFA4211:m (null)] [<private>(<private>)] Failed to start plugin; pkd returned an error: Error Domain=PlugInKit Code=4 "RBSLaunchRequest error trying to launch plugin com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211): Error Domain=RBSRequestErrorDomain Code=5 "Launch failed." UserInfo={NSLocalizedFailureReason=Launch failed., NSUnderlyingError=0x15b324870 {Error Domain=NSPOSIXErrorDomain Code=111 "Unknown error: 111" UserInfo={NSLocalizedDescription=Launchd job spawn failed}}}" UserInfo={NSLocalizedDescription=RBSLaunchRequest error trying to launch plugin com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211): Error Domain=RBSRequestErrorDomain Code=5 "Launch failed." UserInfo={NSLocalizedFailureReason=Launch failed., NSUnderlyingError=0x15b324870 {Error Domain=NSPOSIXErrorDomain Code=111 "Unknown error: 111" UserInfo={NSLocalizedDescription=Launchd job spawn failed}}}}
error 09:13:40.512643+0200 neagent Plugin <private> must have pid! Extension request will fail
error 09:13:40.512675+0200 neagent Failed to aquire assertion for plugin: <private> pid: 0
error 09:13:40.512742+0200 neagent Unable to acquire process assertion in beginUsing: with plugin identifier: <private>, killing plugin
error 09:13:40.512772+0200 neagent begin extension request <private> complete with error: Error Domain=PlugInKit Code=4 UserInfo={NSLocalizedDescription=<private>}
error 09:13:40.512904+0200 neagent PlugInKit error in beginUsing: with plugin identifier: <private>, killing plugin
default 09:13:40.512908+0200 neagent Extension request with extension com.microsoft.AzureVpnMac.PacketTunnel started with identifier (null)
error 09:13:40.513154+0200 neagent Failed to start extension com.microsoft.AzureVpnMac.PacketTunnel: Error Domain=PlugInKit Code=4 "RBSLaunchRequest error trying to launch plugin com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211): Error Domain=RBSRequestErrorDomain Code=5 "Launch failed." UserInfo={NSLocalizedFailureReason=Launch failed., NSUnderlyingError=0x15b324870 {Error Domain=NSPOSIXErrorDomain Code=111 "Unknown error: 111" UserInfo={NSLocalizedDescription=Launchd job spawn failed}}}" UserInfo={NSLocalizedDescription=RBSLaunchRequest error trying to launch plugin com.microsoft.AzureVpnMac.PacketTunnel(767B26BD-D966-4021-8D56-322B7BFA4211): Error Domain=RBSRequestErrorDomain Code=5 "Launch failed." UserInfo={NSLocalizedFailureReason=Launch failed., NSUnderlyingError=0x15b324870 {Error Domain=NSPOSIXErrorDomain Code=111 "Unknown error: 111" UserInfo={NSLocalizedDescription=Launchd job spawn failed}}}}

Thank you for your help so far, hopefully this information leads to a solution.

ChaitanyaNaykodi-MSFT 22,776 Reputation points Microsoft Employee

2023-05-15T16:03:41.52+00:00

@Air2

Thank you for sharing the additional details here.

Based on the error above looks like the com.microsoft.AzureVpnMac.PacketTunnel extension failed launch. This issue can be caused by MDM profiles installed on the user’s device. To verify this is the cause, on your mac device open “System Preferences” -> “Profiles”. Look through all the profiles and check if any of them contains the NSExtension restriction.
If the NSExtension is present and these MDM profiles are managed by your IT team. You can contact them to either remove the policy or add a rule to make exception for this app extension. Since the app extension’s full identifier changes with each version, it is important for the exception rule to be more generic to account for this (e.g. allow all Extension points that start with “com.microsoft.AzureVpnMac”).

Hope this helps. If this does not help resolve the issue, can you please send an email as requested in my answer above? as this issue will require a deeper investigation via a support request.

Thank you!
Air2 35 Reputation points

2023-05-15T16:26:17.6266667+00:00

Hello, thank you for your help! There are not profiles installed at all. So I have send an e-mail as mentioned in your earlier comment.

David Pulley 0 Reputation points

2023-05-22T15:00:09.52+00:00

I have the same issue

I have an brand new out of the box MacBook Pro M2 and once first logged in and signed into my apple ID the first thing i do is put the Azure VPN so I can connect it to the work domain but I get stummped by the same issue

This is not on just one mac I have half a dozen with the same issue, The older mac with Intel chip work just fine
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ChaitanyaNaykodi-MSFT 22,776 Reputation points Microsoft Employee

2023-05-22T18:27:48.4233333+00:00

@David Pulley

Thank you for reaching out. The issue described above is currently being worked on by the Azure Support team, I will post an update here as soon as resolution is achieved. Thank you! Please let us know if you have any further questions.

Nikita Gudiev 0 Reputation points

2024-03-04T13:47:21.7+00:00

I have same issue,
I have manually installed Resetta 2 from the terminal, marked in Azure VPN settings "Open witch Rosetta" and there is the same issue. Azure VPN is connecting after adding my credentials from Azure AD and disconnects after 15 seconds nearly.
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