Ok - Eyeball. On the test environment everything is the same - same cisco IOS, same config, same server 2003 r1 sp2. When you say "so once it has the first address, is on the VLAN and then releases it it cannot then obtain the second address?" that's not correct. When the device has been unplugged and plugged in again, it fails at the first step, because the address which is now offered the FIRST time is the address which was offered the SECOND time previously. Then the cisco router further down (which is transitting the dhcp offer) matches that address in it's config and applies a layer 2 tag, which prevents the device from seeing the offer. Basically the DHCP server seems to ignore the IP address from the ip-helper in the DHCP discovery which should enable it to choose which scope to pick from, and instead use the mac address which it now knows, and choses from the wrong (at that time) scope. In my test environment, even though the previous lease was not released when the device was rebooted, the server behaves correctly, and issues from the scope as per the ip-helper address in the dhcp discovery. Stoic Joker, the device is PoE so when the cable is removed and reinserted, the device boots from fresh and kicks off the original process.