Migrated VPN Service Broken with Catalina

My Mac mini has been working just fine with macOS Mojave as a VPN server following the migration method described in https://developer.apple.com/support/downloads/macOS-Server-Service-Migration-Guide.pdf , but after upgrading to macOS Catalina there is trouble:


The VPN clients connect just fine on the internal network, but not on an external network; which makes the VPN server a bit pointless! I can confirm that all was working well with the server running macOS Mojave, and my iOS 13 and iPadOS 13 clients have been connecting just fine; it is the upgrade to macOS Catalina on the server that has caused this problem.


Here are the log entries for a failed connection:





Posted on Oct 11, 2019 9:42 AM

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Posted on Nov 15, 2019 1:54 AM

I have tried VPN Enabler mention by lcrooks earlier and have managed to get the connection working back to my Catalina OS Mac Mini. I have done this locally from another desktop and remotely from my iphone. The later needed the OpenVPN app installed.

I also needed to edit the config file created by VPN Enabler as it didn't want to work by default. This was a bit of trial and error really as I am certainly no expert on this, but noticed when using the client part of VPN Enabler that the config file didn't seem to reference my server url but the port number instead. I simply replaced the port number with my url and it worked. The lines I changed are below


<key>RemoteAddress</key>

<string>xxx.ddns.net</string> This simply contained "REMOTE"


<key>remote</key>

<string>xxx.ddns.net</string> Note: this is where the port number 1194 was


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120 replies

Jun 25, 2020 1:45 AM in response to lcrooks

I watched the WWDC presentation and paused the video to see just enough: Apple have ported their apps for Apple Silicon and there was definitely a Server icon there, but interestingly no AirPort Utility.


I can almost guarantee you that Big Sur will not fix this VPN issue and I suspect it will break even more services;

There will be more stringent protections of the operating system storage location which will likely prevent editing configuration files for the POSIX services. I was also interested to see the promotion of virtualisation for Apple Silicone and Big Sur. A demonstration included Parallels Desktop running a Debian 10 virtual machine along with the explanation that developers can start a web server in Linux and see it in Safari; this is significant because web services were included in the macOS Server migration guide before the release of macOS Mojave.

Using Parallels Desktop Pro you can run entire operating systems as a system service that starts when the Mac boots, so this would seem to be the preferred way to run servers on a Mac. If you bridge the network for your server vm it appears on the as a separate machine with its own IP address.

I am seriously thinking of getting an Apple Silicon Mac mini when it is eventually released to run all my servers in virtual environments to reduce power consumption. macOS Big Sur and a virtualisation solution might be like having your own little Azure: just make sure you've got plenty of RAM!

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Migrated VPN Service Broken with Catalina

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