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

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https://bugs.launchpad.net/bugs/1472055

Title:
  /etc/network/interfaces up, post-up commands not run at network
  startup

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