Hi Andrew,
Have you checked the phone is pointing to the relevant TFTP Server(s) you have updated (i.e. Option 150), it's not very common to enable TFTP on Subs, usuall the Pub or 1 or more dedicated TFTP Server nodes.
Assuming you are running UCM 8.0 or greater, there is a chance the reason you cannot upgrade firmware is due to an ITL Issue on some phones. When there is more than one TFTP Service in a cluster there is a chance of getting issues with ITL files due to certificate syncronisation delays between TFTP Servers.
If you browse to one of the phones that are not updating and check the 'Status Messages' to see if there are any issues updating the ITL File. If there are update issues then try deleting the ITL File on the phone to see if the allows the firmware upgrade to start.
As there is a possability you have ITL Issues, and you mension the need to update phone background images you should have a look at our product - PhoneView from UnifiedFX
PhoneView can detect and solve ITL issues very easily, update phone backrounds in bulk (without having to update file on the TFTP Server for most phone models) as well a whole host of other features.
Thanks
Stephen Welsh
http://www.unifiedfx.com