VPN is not functional after updating the Monterey

I'm using the L2TP VPN to connect to my workstation LAN.

The VPN connection is fine and I can ping to the local address.

However, I cannot use ssh, and any other tools to access the local LAN anymore after updating.

The device is 16G M1 MacBook Air

Posted on Nov 4, 2021 12:55 AM

Similar questions

built-in vpn (L2TP over IPSec) not working with Monterey Please forgive me if I leave out crucial information in this post - it is my first to the community. I just upgraded to the new 14" MacBook pro (M1 Pro), which is running macOS 12.0.1. I work in education, and my employer provides a VPN server to allow off-site access to certain resources. This was working fine on my old MacBook pro using the built-in VPN client (L2TP over IPSec). On Monterey, I am still able to authenticate with the VPN server, and it shows that I am connected. However, when I try to access or even ping a resource that should be available via the VPN, it fails (Request timeout for a ping). The rest of the internet still functions as usual. My IT department believes that iCloud private relay could be the issue. However, I do not use iCloud, and rather than having an "options button" in System Preferences -> Apple ID -> iCloud -> Private Relay I have an "upgrade" button. Everything is unchecked within Apple ID. Any suggestions on how to get the built-in VPN client to function, or 3rd party alternatives that would allow me to connect via L2TP over IPSec, would be welcome. [Edited by Moderator]
9874 6
L2TP IPSec VPN failures after upgrade to MacOS Big Sur After upgrading to Big Sur (from up-to-date Caralina) this week I discovered half of my VPN connections to remote sites are no longer working. The error is the "L2TP-VPN server did not respond" .. however pretty sure you get the same error if the shared secret is mis-matched. All VPN connections continue to work as before from Windows 10. Target VPN servers are Draytek Vigor ADSL routers I've tried manually re-created the VPN configuration on the Mac, but no luck. The only thing I can think of is an incompatibility between certain models of Draytek router with BigSur. I've seen people reporting problems with Big Sur beta releases but no fixes. Anyone else with similar? Thanks
3997 2
Shared vpn not working I have PureVPN installed on my MacBook Pro. I have followed all instructions to share my connection to my ps5. MacBook is connected to wifi ps5 is connected via Ethernet. All works and I have an internet connection however my vpn is not being shared over this connection like it should be. If I do an ip location check on ps5 it shows true location if I do it on my MacBook it shows my chosen vpn ip. Is there something I’m missing ?? Cheers.
1050 1

1 reply

SnickZ.

Community Specialist

Nov 5, 2021 6:07 AM in response to yifu240

Hi yifu240,

Thanks for using Apple Support Communities. We understand that you're having some issues with your VPN connection after the macOS Monterey update. You'll want to make sure that the options/preferences for L2TP are correct. Check out the following articles.

Set up a VPN connection on Mac

Change options for L2TP over IPSec VPN connections on Mac

Take care.

This thread has been closed by the system or the community team. You may vote for any posts you find helpful, or search the Community for additional answers.

VPN is not functional after updating the Monterey

Welcome to Apple Support Community

A forum where Apple customers help each other with their products. Get started with your Apple Account.

Learn more Sign up