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

Oct 31, 2019 1:06 PM in response to TrainsAndWellbeing

Hi Everyone,


The very intrepid Bernard Tao of VPN Enabler may have come up with a solution. I have already rolled back to Mjoave, but if someone is brave enough to try and test his solution, I would be eternally grateful! I am not going to upgrade Catalina until we have a 100% solution for this massive problem. Loss of VPN is incredibly disruptive to my workflow.


http://cutedgesystems.com/software/openvpnenablerforcatalina/


Thanks!

Jan 13, 2020 5:47 PM in response to Machist

I could no longer wait for Apple to fix this solution.


I ended up purchasing a Cisco RV325 VPN Router and installed it in our office so that I could reach macOS Server, all of the machines on the network and all of the services. It actually works a thousand times better than the software VPN that macOS Server provided in the past as you basically have unlimited control with monitoring of who accesses your network.

Jan 15, 2020 2:45 PM in response to lcrooks

macOS vpnd L2TP configuration uses four things:

  1. macOS networking and firewall (pf, application) infrastructure
  2. The /usr/sbin/vpnd binary
  3. The config file /Library/Preferences/SystemConfiguration/com.apple.RemoteAccessServers.plist
  4. The PSK in the System Keychain in the entry com.apple.net.racoon


MacPorts uses an example config file (based on the old Server.app one), here: https://github.com/macports/macports-ports/blob/master/net/macos-vpn-server/files/com.apple.RemoteAccessServers.plist.macports


The Portfile shows how to add the PSK to the Keychain, here: https://github.com/macports/macports-ports/blob/f16847defa1b99199baf0a569d2fbeb36a8f908f/net/macos-vpn-server/Portfile#L56


/usr/bin/security add-generic-password -a org.macports.ppp.l2tp -s com.apple.net.racoon -T /usr/sbin/racoon -w ${vpn_pre_shared_secret} -U /Library/Keychains/System.keychain

May 21, 2020 9:44 AM in response to TrainsAndWellbeing

My hats off to all of the highly ingenious 3rd party solutions but one of the key reasons many of us bought a mac mini was to have a simple, integrated, Apple-ecosystem-centric solution to home networking. The fact that Apple has unnecessarily rendered their software solution into obsolescence is highly malicious towards their own customers. Frankly, it is unacceptable and should be "fixed" by Apple. I know that Apple could care less what we think, but I would advocate that we maintain pressure. I can say with 100% certainty this will be my last mac if Apple continues to be so obtuse and unwilling to listen to their own loyal customers.

Jun 16, 2020 6:59 PM in response to mini-bob

Hello All- just stumbled upon this thread after experiencing the same issues still in (2020 June)- unfortunately I'm not a networking /IT expert. I am using both the Sophos connect and OpenVPN connect to connect remotely to our company's VPN. These are my 'lay-person' experiences for both clients-

  1. Unable to connect to work VPN after upgrading to Catalina.
  2. All devices unable to connect following Catalina Update (Macbook 12", MacBookPro 15" (2013), MacbookPro16" (2019)
  3. However - iPadPro2018 appears to connect just fine
  4. Home setup comprises of a Router (provided by service provider) and a AirPort Extreme in another bedroom as wifi extender.
    1. Somehow - I managed to get it to 'sort-of'* work after forcing my MacBook to 'forget' the wifi extender (Apple AirPort Extreme)
    2. *sort-of > connection stutters about about 10-15mins but doesn't connection does not drop.


Hopefully there is a solution for this- hopefully will be addressed soon with WWDC coming up!

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Migrated VPN Service Broken with Catalina

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