We are using wireless OTA enterprise activation. He does have the correct data plan. He has checked several times with the provider to make certain that he is using a Blackberry Enterprise data plan. Our people in Italy even checked with us before purchasing the Bold which data plan they should get. I know he received a new SIM with the Blackberry, and the provider is telling him that everything is set up properly.
The funny thing is that Blackberries in Europe has been hit or miss. We had one in our Swiss office have the same problem, but the next time they got a new Blackberry it activated just fine.