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 (Beta) 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.

Answered by gbarnes1 in 701099022

This question has been answered here: https://discussions.apple.com/thread/253312106 but I do believe it means that all traffic will be sent over the VPN even if not strictly necessary?

I also got the problem with vpn L2TP Over IPsec after upgrade to Monterey. It work fine with Big Sur 11.6, but after upgrade to Monterey 12.0.1, after VPN connected, I can ping to my server, but cannot telnet, ssh to server port 22

me too

Me too

Dear Apple support,

I have  Monterey 12.0.1 and I have problems L2TP over IPSEC, it give to that I need to configure PAP or CHAP but on MacBook Pro (13-inch, M1, 2020) I can not configure any PAP and CHAP. Can you please help me

I have similar problem with my 14'' Macbook Pro. My office VPN server setup doesn't have IPSec so I have the following in my /etc/ppp/options

plugin L2TP.ppp
l2tpnoipsec

I can connect to the server, and ping internal hosts, but ssh or curl would timeout. The problem still exists on 12.1.

I have filed a bug but no feedback yet (FB9810608).

I have found a workaround for me, according to https://discussionschinese.apple.com/thread/253302896?answerId=256624128322#256624128322

Turn off your WiFi on you MacBook, connect to your iPhone over physical cable and turn on personal hotspot on your iPhone.

Accepted Answer

This question has been answered here: https://discussions.apple.com/thread/253312106 but I do believe it means that all traffic will be sent over the VPN even if not strictly necessary?

I contacted Apple support and restarted the Mac in safe mode, where the VPN worked, then back to normal mode and the VPN worked fine.

built-in vpn (L2TP over IPSec) not working with Monterey
 
 
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