There is no reason at all why he cannot activate from Italy against a US BES.
I have a UK BES, and have activated users in Canada, USA, Europe and India against it.
When he got the Bold, did he get a new SIM? I am wondering whether the Bold is provisioned with the right data plan....
: Groupware Infrastructure Architect, Denver CO If I'm not here, I'm playing World's End on FaceBook. Mob/Mafia Wars are SOO last year