I've managed to get the update to work by doing a small batch at a time. The update button was puking at the sheer number of updates it looked like. So using a combination of the Zentyal interface and the the CLI when that started complaining everything is reporting that its all updated.
Unfortunately, I can not connect to the VPN now. I re-issued the certs just to be sure it wasn't something there. There is no error in the interface, it just won't connect, here's the log:
Mon Nov 26 13:32:39 2018 OpenVPN 2.3.2 i686-w64-mingw32 [SSL (OpenSSL)] [LZO] [PKCS11] [eurephia] [IPv6] built on Aug 22 2013
Enter Management Password:
Mon Nov 26 13:32:39 2018 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:25340
Mon Nov 26 13:32:39 2018 Need hold release from management interface, waiting...
Mon Nov 26 13:32:40 2018 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:25340
Mon Nov 26 13:32:40 2018 MANAGEMENT: CMD 'state on'
Mon Nov 26 13:32:40 2018 MANAGEMENT: CMD 'log all on'
Mon Nov 26 13:32:40 2018 MANAGEMENT: CMD 'hold off'
Mon Nov 26 13:32:40 2018 MANAGEMENT: CMD 'hold release'
Mon Nov 26 13:32:40 2018 Socket Buffers: R=[65536->65536] S=[65536->65536]
Mon Nov 26 13:32:40 2018 UDPv4 link local: [undef]
Mon Nov 26 13:32:40 2018 UDPv4 link remote: [AF_INET]<PUBLIC IP AND PORT FOR VPN>
Mon Nov 26 13:32:40 2018 MANAGEMENT: >STATE:1543257160,WAIT,,,
Mon Nov 26 13:32:40 2018 MANAGEMENT: >STATE:1543257160,AUTH,,,
Mon Nov 26 13:32:40 2018 TLS: Initial packet from [AF_INET]<PUBLIC IP AND PORT FOR VPN>, sid=540847a9 910e6c92
Mon Nov 26 13:32:40 2018 VERIFY OK: depth=1, C=CA, ST=Undefined, L=Gatineau, O=company Inc., CN=company Inc. Authority Certificate
Mon Nov 26 13:32:40 2018 VERIFY X509NAME OK: C=CA, ST=Undefined, L=Gatineau, O=company Inc., CN=vpn-company.company.com
Mon Nov 26 13:32:40 2018 VERIFY OK: depth=0, C=CA, ST=Undefined, L=Gatineau, O=Oproma Inc., CN=vpn-company.company.com
Mon Nov 26 13:33:33 2018 SIGTERM received, sending exit notification to peer
Mon Nov 26 13:33:37 2018 SIGTERM[soft,exit-with-notification] received, process exiting
Mon Nov 26 13:33:37 2018 MANAGEMENT: >STATE:1543257217,EXITING,exit-with-notification,,
I've removed any identifiable information from the above. Nothing else has changed although I did notice that the interface for our OTHER internal OpenVPN (that works) is showing the
VPN interface address 10.10.100.1/32
While the other one that has been updated has NO information in that section. I did not see how to add it.