I had the same issue until I upgraded my AD Schema to Server 2008 R2 (I didn't have to upgrade any DC's).
We've deployed some printers with Group Policy and assigned them per-computer in the GPO. In the same GPO we removed an existing printer. When we test it on a Windows 7 system, when we login, nothing changes.
From our Group Policy Management console, we noticed that running a RSOP shows the same thing, all the same printers are there. We ran GPupdate /force and now a RSOP shows the new printer as well as the old printer gone. Checking the client machine, under Devices and Printers, the only changes are that the old printer has been removed, no sign of the new printer.
We always thought that with per-compute printer, you had to actually reboot to get the thing installed. Today I read a Technet article that gave me some hope (Deploy Printer Connections ) It says that "For per-computer connections, Windows adds the printer connections when the user logs on."
Why isn't this happening when I logon?
I had the same issue until I upgraded my AD Schema to Server 2008 R2 (I didn't have to upgrade any DC's).