Can you show "systemctl status openvpn-server@first.service" and "systemctl status openvpn-server@second.service", both before and after the restart?
Actually, the whole directory seems to be removed as it gets a new inode number. Note that first I have to completely restart "first" and then restart "second".
This is the complete sequence of commands I ran, including the requested information. # ls -di /run/openvpn-server 13067 /run/openvpn-server # ls /run/openvpn-server status-first.log status-second.log # systemctl status openvpn-server@first.service ● openvpn-server@first.service - OpenVPN service for first Loaded: loaded (/lib/systemd/system/openvpn-server@.service; enabled; vendor preset: enabled) Active: active (running) since Tue 2017-10-10 05:42:12 UTC; 54s ago Docs: man:openvpn(8) https://community.openvpn.net/openvpn/wiki/Openvpn24ManPage https://community.openvpn.net/openvpn/wiki/HOWTO Main PID: 1361 (openvpn) Status: "Initialization Sequence Completed" Tasks: 1 (limit: 4915) CGroup: /system.slice/system-openvpn\x2dserver.slice/openvpn-server@first.service └─1361 /usr/sbin/openvpn --status /run/openvpn-server/status-first.log --status-version 2 --suppress-timestamps --config first.conf Oct 10 05:42:12 box openvpn[1361]: WARNING: --keepalive option is missing from server config Oct 10 05:42:12 box openvpn[1361]: NOTE: the current --script-security setting may allow this configuration to call user-defined scripts Oct 10 05:42:12 box openvpn[1361]: TUN/TAP device tap9 opened Oct 10 05:42:12 box openvpn[1361]: Could not determine IPv4/IPv6 protocol. Using AF_INET Oct 10 05:42:12 box openvpn[1361]: UDPv4 link local (bound): [AF_INET][undef]:12345 Oct 10 05:42:12 box openvpn[1361]: UDPv4 link remote: [AF_UNSPEC] Oct 10 05:42:12 box openvpn[1361]: GID set to nogroup Oct 10 05:42:12 box systemd[1]: Started OpenVPN service for first. Oct 10 05:42:12 box openvpn[1361]: UID set to nobody Oct 10 05:42:12 box openvpn[1361]: Initialization Sequence Completed # systemctl status openvpn-server@second.service ● openvpn-server@second.service - OpenVPN service for second Loaded: loaded (/lib/systemd/system/openvpn-server@.service; enabled; vendor preset: enabled) Active: active (running) since Tue 2017-10-10 05:42:22 UTC; 3min 49s ago Docs: man:openvpn(8) https://community.openvpn.net/openvpn/wiki/Openvpn24ManPage https://community.openvpn.net/openvpn/wiki/HOWTO Main PID: 1407 (openvpn) Status: "Initialization Sequence Completed" Tasks: 1 (limit: 4915) CGroup: /system.slice/system-openvpn\x2dserver.slice/openvpn-server@second.service └─1407 /usr/sbin/openvpn --status /run/openvpn-server/status-second.log --status-version 2 --suppress-timestamps --config second.conf Oct 10 05:42:22 box openvpn[1407]: WARNING: --keepalive option is missing from server config Oct 10 05:42:22 box openvpn[1407]: NOTE: the current --script-security setting may allow this configuration to call user-defined scripts Oct 10 05:42:22 box openvpn[1407]: TUN/TAP device tap8 opened Oct 10 05:42:22 box openvpn[1407]: Could not determine IPv4/IPv6 protocol. Using AF_INET Oct 10 05:42:22 box openvpn[1407]: UDPv4 link local (bound): [AF_INET][undef]:12346 Oct 10 05:42:22 box openvpn[1407]: UDPv4 link remote: [AF_UNSPEC] Oct 10 05:42:22 box openvpn[1407]: GID set to nogroup Oct 10 05:42:22 box openvpn[1407]: UID set to nobody Oct 10 05:42:22 box openvpn[1407]: Initialization Sequence Completed Oct 10 05:42:22 box systemd[1]: Started OpenVPN service for second. # systemctl restart openvpn-server@first # systemctl restart openvpn-server@second # ls -di /run/openvpn-server 20235 /run/openvpn-server # ls /run/openvpn-server status-second.log # systemctl status openvpn-server@first.service ● openvpn-server@first.service - OpenVPN service for first Loaded: loaded (/lib/systemd/system/openvpn-server@.service; enabled; vendor preset: enabled) Active: active (running) since Tue 2017-10-10 05:47:01 UTC; 3min 46s ago Docs: man:openvpn(8) https://community.openvpn.net/openvpn/wiki/Openvpn24ManPage https://community.openvpn.net/openvpn/wiki/HOWTO Main PID: 1488 (openvpn) Status: "Initialization Sequence Completed" Tasks: 1 (limit: 4915) CGroup: /system.slice/system-openvpn\x2dserver.slice/openvpn-server@first.service └─1488 /usr/sbin/openvpn --status /run/openvpn-server/status-first.log --status-version 2 --suppress-timestamps --config first.conf Oct 10 05:47:01 box openvpn[1488]: WARNING: --keepalive option is missing from server config Oct 10 05:47:01 box openvpn[1488]: NOTE: the current --script-security setting may allow this configuration to call user-defined scripts Oct 10 05:47:01 box openvpn[1488]: TUN/TAP device tap9 opened Oct 10 05:47:01 box openvpn[1488]: Could not determine IPv4/IPv6 protocol. Using AF_INET Oct 10 05:47:01 box openvpn[1488]: UDPv4 link local (bound): [AF_INET][undef]:12345 Oct 10 05:47:01 box openvpn[1488]: UDPv4 link remote: [AF_UNSPEC] Oct 10 05:47:01 box systemd[1]: Started OpenVPN service for first. Oct 10 05:47:01 box openvpn[1488]: GID set to nogroup Oct 10 05:47:01 box openvpn[1488]: UID set to nobody Oct 10 05:47:01 box openvpn[1488]: Initialization Sequence Completed # systemctl status openvpn-server@second.service ● openvpn-server@second.service - OpenVPN service for second Loaded: loaded (/lib/systemd/system/openvpn-server@.service; enabled; vendor preset: enabled) Active: active (running) since Tue 2017-10-10 05:47:04 UTC; 4min 3s ago Docs: man:openvpn(8) https://community.openvpn.net/openvpn/wiki/Openvpn24ManPage https://community.openvpn.net/openvpn/wiki/HOWTO Main PID: 1503 (openvpn) Status: "Initialization Sequence Completed" Tasks: 1 (limit: 4915) CGroup: /system.slice/system-openvpn\x2dserver.slice/openvpn-server@second.service └─1503 /usr/sbin/openvpn --status /run/openvpn-server/status-second.log --status-version 2 --suppress-timestamps --config second.conf Oct 10 05:47:04 box openvpn[1503]: WARNING: --keepalive option is missing from server config Oct 10 05:47:04 box openvpn[1503]: NOTE: the current --script-security setting may allow this configuration to call user-defined scripts Oct 10 05:47:04 box openvpn[1503]: TUN/TAP device tap8 opened Oct 10 05:47:04 box openvpn[1503]: Could not determine IPv4/IPv6 protocol. Using AF_INET Oct 10 05:47:04 box openvpn[1503]: UDPv4 link local (bound): [AF_INET][undef]:12346 Oct 10 05:47:04 box openvpn[1503]: UDPv4 link remote: [AF_UNSPEC] Oct 10 05:47:04 box openvpn[1503]: GID set to nogroup Oct 10 05:47:04 box openvpn[1503]: UID set to nobody Oct 10 05:47:04 box openvpn[1503]: Initialization Sequence Completed Oct 10 05:47:04 box systemd[1]: Started OpenVPN service for second.