Simon, The setup I have is running two OpenVPN daemons on the same port (1618) but on different protocols (TCP/UDP). The post that Chris made in the AWS forum above had a much simpler, single virtual interface setup. root@ip-10-0-0-9:~# ip addr 1: lo: mtu 65536 qdisc noqueue state UNKNOWN group default qlen 1 link/loopback 00:00:00:00:00:00 brd 00:00:00:00:00:00 inet 127.0.0.1/8 scope host lo valid_lft forever preferred_lft forever inet6 ::1/128 scope host valid_lft forever preferred_lft forever 2: eth0: mtu 9001 qdisc pfifo_fast state UP group default qlen 1000 link/ether 06:cc:43:0f:66:e9 brd ff:ff:ff:ff:ff:ff inet 10.0.0.9/28 brd 10.0.0.15 scope global eth0 valid_lft forever preferred_lft forever inet6 fe80::4cc:43ff:fe0f:66e9/64 scope link valid_lft forever preferred_lft forever 3: tun0: mtu 1500 qdisc pfifo_fast state UNKNOWN group default qlen 100 link/none inet 10.255.248.1/23 brd 10.255.249.255 scope global tun0 valid_lft forever preferred_lft forever 4: tun1: mtu 1500 qdisc pfifo_fast state UNKNOWN group default qlen 100 link/none inet 10.255.250.1/23 brd 10.255.251.255 scope global tun1 valid_lft forever preferred_lft forever root@ip-10-0-0-9:~# ip route default via 10.0.0.1 dev eth0 10.0.0.0/28 dev eth0 proto kernel scope link src 10.0.0.9 10.255.248.0/23 dev tun0 proto kernel scope link src 10.255.248.1 10.255.250.0/23 dev tun1 proto kernel scope link src 10.255.250.1 root@ip-10-0-0-9:~# netstat -nlp Active Internet connections (only servers) Proto Recv-Q Send-Q Local Address Foreign Address State PID/Program name tcp 0 0 0.0.0.0:1618 0.0.0.0:* LISTEN 2875/openvpn tcp 0 0 0.0.0.0:22 0.0.0.0:* LISTEN 1059/sshd tcp6 0 0 :::22 :::* LISTEN 1059/sshd udp 0 0 0.0.0.0:68 0.0.0.0:* 876/dhclient udp 0 0 0.0.0.0:1618 0.0.0.0:* 2874/openvpn Active UNIX domain sockets (only servers) Proto RefCnt Flags Type State I-Node PID/Program name Path unix 2 [ ACC ] STREAM LISTENING 8782 1/init /run/lvm/lvmpolld.socket unix 2 [ ACC ] STREAM LISTENING 20818 2974/systemd /run/user/1000/systemd/private unix 2 [ ACC ] SEQPACKET LISTENING 8864 1/init /run/udev/control unix 2 [ ACC ] STREAM LISTENING 8783 1/init /run/systemd/journal/stdout unix 2 [ ACC ] STREAM LISTENING 9033 1/init /run/lvm/lvmetad.socket unix 2 [ ACC ] STREAM LISTENING 10909 1/init /run/acpid.socket unix 2 [ ACC ] STREAM LISTENING 20850 3012/0 /tmp/ssh-zhPNN6x7d9/agent.3012 unix 2 [ ACC ] STREAM LISTENING 10899 1/init /run/snapd.socket unix 2 [ ACC ] STREAM LISTENING 10824 1/init /var/run/dbus/system_bus_socket unix 2 [ ACC ] STREAM LISTENING 10891 1/init /run/uuidd/request unix 2 [ ACC ] STREAM LISTENING 10893 1/init /var/lib/lxd/unix.socket unix 2 [ ACC ] STREAM LISTENING 13922 1074/iscsid @ISCSIADM_ABSTRACT_NAMESPACE unix 2 [ ACC ] STREAM LISTENING 17650 1/init /var/run/pcscd/pcscd.comm unix 2 [ ACC ] STREAM LISTENING 8778 1/init /run/systemd/private