Sorry - can you clarify the problem? I think I understand, but just to make sure... Are you saying you can license your 3300 ICP via the Software Installer Tool, but when it comes to updating the licensing from the actual licensing form with the 3300 ICP, it fails...???
If that's the case:
A) Ensure the 3300 can access the Internet (from it's VLAN). Make sure there is a route in place so the 3300 ICP (and other Mitel servers on the voice VLAN) can access the Internet.
B) Ensure the DNS entries (i.e. DNS servers) are setup properly on your 3300 ICP. It won't work if you don't have DNS setup and setup properly.
C) Using the ping command on the 3300, make sure you can ping FQDNs of your choice on the public Internet (whatever is on the Internet and can be pinged).
If you can do all of that (A-C) then you should be able to license via the AMC right from the 3300 ICP. If you can't, however you can successful ping FQDNs from the 3300 ICP on the Internet, then you probably have a firewall blocking problem and you should look at your firewall. As a side note, most firewalls support AMC licensing synchronization, but there is a few that don't support this with the base configuration. I can't think of any specific firewall manufactures off the top of my head that block this, but I have had to ask Network Administrators to make changes so the 3300 ICP (and other Mitel software servers) can access the AMC. More often then not, it's not the firewall's default policies that are blocking this as much as it is Network Administrators that want to make everything secure, but they don't know how to do that properly, so they create network (IP, port, routing rules) policies that block everything (that's just my experience).
Let us know how you make out.