Not sure if this will help, but here's how I did it on my server (don't pay attention to the wrong addresses or masks...): auto eth0 iface eth0 inet static address 192.168.1.31 netmask 255.255.240.0 gateway 192.168.1.1 up route add -host 192.168.1.31 dev eth0 pre-up iptables-restore < /etc/iptables.rules auto eth0:1 iface eth0:1 inet static address 192.168.1.32 netmask 255.255.240.0 gateway 192.168.1.1 up route add -host 192.168.1.32 dev eth0:1 auto eth0:2 iface eth0:2 inet static address 192.168.1.33 netmask 255.255.240.0 gateway 192.168.1.1 up route add -host 192.168.1.33 dev eth0:2 And somehow, auto eth0:1 ... wouldn't work properly, so i just added the following to /etc/rc.local, to make sure they are brought up: ifup eth0 ifup eth0:1 ifup eth0:2