Peter, I resolved this. I came across a reference to a package available with Ubuntu called ifupdown-extras. It adds a file in /etc/network/ called routes. http://askubuntu.com/questions/168033/how-to-set-static-routes- in-ubuntu-server
I added the package and edited my /etc/network/interfaces to remove the post-up route statements and added them into the /etc/network/routes file as; ## Network for A 10.101.0.0 255.255.240.0 10.100.1.254 eth1 10.100.1.0 255.255.255.248 10.100.1.254 eth1 ## Network for B 10.100.1.24 255.255.255.248 10.100.1.254 eth1 10.114.0.0 255.255.248.0 10.100.1.254 eth1 ## Network for C 10.100.1.16 255.255.255.248 10.100.1.254 eth1 10.113.0.0 255.255.248.0 10.100.1.254 eth1 ## Network for D 10.112.0.0 255.255.240.0 10.100.1.254 eth1 After multiple reboots the routes seem to be working each time. Kernel IP routing table Destination Gateway Genmask Flags MSS Window irtt Iface default 192.168.1.254 0.0.0.0 UG 0 0 0 eth0 10.100.1.0 10.100.1.254 255.255.255.248 UG 0 0 0 eth1 10.100.1.16 10.100.1.254 255.255.255.248 UG 0 0 0 eth1 10.100.1.24 10.100.1.254 255.255.255.248 UG 0 0 0 eth1 10.100.1.248 * 255.255.255.248 U 0 0 0 eth1 10.101.0.0 10.100.1.254 255.255.240.0 UG 0 0 0 eth1 10.112.0.0 10.100.1.254 255.255.240.0 UG 0 0 0 eth1 10.113.0.0 10.100.1.254 255.255.248.0 UG 0 0 0 eth1 10.114.0.0 10.100.1.254 255.255.248.0 UG 0 0 0 eth1 192.168.1.0 * 255.255.255.0 U 0 0 0 eth0 Interesting note. I had a typo in one of the statements and because the gateway was not seen as a local interface, it did not add that route. I'm not sure if this is a workaround or the intended function on Ubuntu's part based on the ifupdown-extra being available. Thought I'd pass it along. David G -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1472055 Title: /etc/network/interfaces up, post-up commands not run at network startup To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/netscript-2.4/+bug/1472055/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs