Yes, based on the extra service name I believe I messed up along the lines of "systemctl enable openvpn" and didn't put in the @configname. What I really don't get is with it disabled openvpn does not work after a reboot. Walking through this:
$ sudo systemctl list-unit-files | grep vpn
[sudo] password for scottjal:
openvpn.service disabled
openvpn@.service disabled
enable, start and check the one I want
$ sudo systemctl enable openvpn@server
Created symlink from /etc/systemd/system/multi-user.target.wants/openvpn@server.service to /lib/systemd/system/openvpn@.service.
$ sudo systemctl start openvpn@server
$ sudo systemctl status openvpn@server
● openvpn@server.service - OpenVPN connection to server
Loaded: loaded (/lib/systemd/system/openvpn@.service; enabled; vendor preset: enabled)
Active: active (running) since Sat 2017-11-11 10:02:42 EST; 7s ago
Docs: man:openvpn(8)
https://community.openvpn.net/openvpn/wiki/Openvpn23ManPage
https://community.openvpn.net/openvpn/wiki/HOWTO
Process: 6834 ExecStart=/usr/sbin/openvpn --daemon ovpn-%i --status /run/openvpn/%i.status 10 --cd /etc/openvpn --script-security 2 --config /etc/openvpn/%i.conf --writepid /run/openvpn/%i.pid (code=exi
Main PID: 6836 (openvpn)
CGroup: /system.slice/system-openvpn.slice/openvpn@server.service
└─6836 /usr/sbin/openvpn --daemon ovpn-server --status /run/openvpn/server.status 10 --cd /etc/openvpn --script-security 2 --config /etc/openvpn/server.conf --writepid /run/openvpn/server.pid
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: TCPv4_SERVER link remote: [undef]
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: MULTI: multi_init called, r=256 v=256
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: IFCONFIG POOL: base=10.8.0.4 size=62, ipv6=0
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: ifconfig_pool_read(), in='client4,10.8.0.4', TODO: IPv6
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: succeeded -> ifconfig_pool_set()
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: IFCONFIG POOL LIST
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: client4,10.8.0.4
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: MULTI: TCP INIT maxclients=1024 maxevents=1028
Nov 11 10:02:42 ubuntuserver ovpn-server[6836]: Initialization Sequence Completed
Nov 11 10:02:42 ubuntuserver systemd[1]: Started OpenVPN connection to server.
At this point I can verify that the VPN works externally through my phone. Other services like SSH, samba shares work etc. BUT if I reboot the server all those things break, SSH won't connect, samba shares won't mount, the VPN will not connect, it's a mess. If I then stop openvpn@server I can SSH again.
Why would this work if I manually start it but not after a reboot with an enabled service?