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.

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gbarnes1
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  • 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

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    programervn

  • me too

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    DenisKuang

  • Me too

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    Jake_Cui
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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?

Posted by
gbarnes1
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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

Posted by
sfiorenza
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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.

Posted by
wangcheng
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  • bro.Any follow-up results?

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    chenhaha

  • @chenhaha sadly no real progress. After communicating back and forth with apple, and providing packet captures, they still need more from me. Unfortunately, I left the company and lost the VPN access. Only if they had replied to me a little sooner...

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    wangcheng
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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?

Posted by
gbarnes1
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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.

Posted by
avalerin-albatros
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