How to fix L2TP VPN connection on Big Sur 11.7.2

I have a working VPN server on Synology NAS. iOS devices v.16.2 can connect without problem, so it should not be a server issue.


But MBP cannot connect since upgrade to Big Sur 11.7.2. Later OS is not compatible.


Message is "The L2TP-VPN server did not respond." Thanks.


Posted on Dec 29, 2022 09:16 PM

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Posted on Dec 31, 2022 03:46 PM

So I worked with Apple and yes it is broken.....that shot me this thread which someone who was running ventura did a solution using Apple Configurator.


L2TP VPN broken on MacOS 13/Ventura | Apple Developer Forums


But there is no place that I can find a legacy version of Apple Configurator version 2.13. If anyone sees a location that is legit please add the link to the thread.


It is pretty crazy that Apple will not let you download the legacy versions of an app.


What's new in Apple Configurator 2.13.3

  • Support for macOS Big Sur
  • Support for restoring macOS on Mac computers with Apple silicon
  • Web Clip: Configure Ignore Manifest Scope and Target Application Bundle Identifier
  • Bug fixes and performance improvements

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5 replies
Question marked as Top-ranking reply

Dec 31, 2022 03:46 PM in response to GreenRiver88

So I worked with Apple and yes it is broken.....that shot me this thread which someone who was running ventura did a solution using Apple Configurator.


L2TP VPN broken on MacOS 13/Ventura | Apple Developer Forums


But there is no place that I can find a legacy version of Apple Configurator version 2.13. If anyone sees a location that is legit please add the link to the thread.


It is pretty crazy that Apple will not let you download the legacy versions of an app.


What's new in Apple Configurator 2.13.3

  • Support for macOS Big Sur
  • Support for restoring macOS on Mac computers with Apple silicon
  • Web Clip: Configure Ignore Manifest Scope and Target Application Bundle Identifier
  • Bug fixes and performance improvements

Dec 29, 2022 09:40 PM in response to ron App

Log (IP address is correctly resolved but replaced with xxxx:


L2TP connecting to server 'xxxx.xxxx.xxx' (xxx.xxx.xxx.xxx)...

L2TP can't set L2TP server address: Cannot allocate memory

IPSec connection started

L2TP error sending Hello (Destination address required)

Failed to send L2TP hello trigger. tried 0, max 10

L2TP error sending Hello (Destination address required)

Failed to send L2TP hello trigger. tried 0, max 10

L2TP error sending Hello (Destination address required)

Failed to send L2TP hello trigger. tried 0, max 10

L2TP error sending Hello (Destination address required)

Failed to send L2TP hello trigger. tried 0, max 10

L2TP error sending Hello (Destination address required)

Failed to send L2TP hello trigger. tried 0, max 10

IPSec connection failed

Dec 31, 2022 09:33 AM in response to ron App

Hi Ron, Yup ....Apple messed something up from 11.7 to 11.7.2 in regards to VPN (L2TP)


I had my buddy test on an older iMac 11.7 and setup the VPN connection identical to what I had on iMAC with 11.7.2 and of course it works. So whatever they did killed the L2TP connection and we are all getting the same error.

Hopefully we can get them to issue a patch. I am not ready to go Ventura (only 3 months old) as there are other compatibility issues and not worth the risk.

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How to fix L2TP VPN connection on Big Sur 11.7.2

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