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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]

MacBook Pro 14″, macOS 12.0

Posted on Oct 30, 2021 8:04 AM

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Question marked as Top-ranking reply

Posted on Nov 19, 2021 6:11 AM

I found a solution for the issues I was facing.

Bought a new MacBook Air with Apple M1 chip and migrated the MacBook from old to new. VPN and Microsoft RDP worked flawlessly on my old Mac, but didn't work at the new MacBook; exact same settings for VPN and RDP.

I had my IT guy look at it and he found a solution:

in Mac > Settings > Network you see the circle with three dots in the bottom left > set order .... (I have Dutch language, so not sure what it is in English) and change the order to have VPN on top, above wifi/Lan. 

This worked for me!

Similar questions

6 replies
Question marked as Top-ranking reply

Nov 19, 2021 6:11 AM in response to gbarnes1

I found a solution for the issues I was facing.

Bought a new MacBook Air with Apple M1 chip and migrated the MacBook from old to new. VPN and Microsoft RDP worked flawlessly on my old Mac, but didn't work at the new MacBook; exact same settings for VPN and RDP.

I had my IT guy look at it and he found a solution:

in Mac > Settings > Network you see the circle with three dots in the bottom left > set order .... (I have Dutch language, so not sure what it is in English) and change the order to have VPN on top, above wifi/Lan. 

This worked for me!

Nov 1, 2021 6:43 AM in response to gbarnes1

Big Sur already suffered some VPN issues. I guess with Monterey is more-less the same.


Unfortunately, I can't offer you a solution – I report you, though, some links addressing a similar issue. Hope you'll find it useful:


https://medium.com/macos-sh/big-sur-l2tp-vpn-blues-7a1b6a2d5a81

https://discussions.apple.com/thread/252366189

https://www.reddit.com/r/MacOSBeta/comments/ih22h9/vpn_l2tp_over_ipsec_stopped_working_after/


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

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