I finally got to confirm this. I had to install ntp to see the same problem in my vm. Before that, openvpn was always running after a reboot.
The moment I installed ntp and rebooted, I got the issue: Mon Nov 20 19:17:41 2017 TCP/UDP: Socket bind failed on local address [AF_INET]10.0.6.10:1194: Cannot assign requested address Mon Nov 20 19:17:41 2017 Exiting due to fatal error root@04-57:~# systemctl status [email protected] ● [email protected] - OpenVPN connection to server Loaded: loaded (/lib/systemd/system/[email protected]; disabled; vendor preset: enabled) Active: failed (Result: exit-code) since Mon 2017-11-20 19:17:41 UTC; 1min 30s ago Docs: man:openvpn(8) https://community.openvpn.net/openvpn/wiki/Openvpn23ManPage https://community.openvpn.net/openvpn/wiki/HOWTO Process: 577 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=exited, sta Main PID: 612 (code=exited, status=1/FAILURE) Nov 20 19:17:41 04-57 systemd[1]: Starting OpenVPN connection to server... Nov 20 19:17:41 04-57 systemd[1]: Started OpenVPN connection to server. Nov 20 19:17:41 04-57 systemd[1]: [email protected]: Main process exited, code=exited, status=1/FAILURE Nov 20 19:17:41 04-57 systemd[1]: [email protected]: Unit entered failed state. Nov 20 19:17:41 04-57 systemd[1]: [email protected]: Failed with result 'exit-code'. lines 1-14/14 (END) -- You received this bug notification because you are a member of Ubuntu Server Team, which is subscribed to the bug report. https://bugs.launchpad.net/bugs/1689833 Title: OpenVPN server does not start properly on boot To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openvpn/+bug/1689833/+subscriptions -- Ubuntu-server-bugs mailing list [email protected] Modify settings or unsubscribe at: https://lists.ubuntu.com/mailman/listinfo/ubuntu-server-bugs
