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Two things seem to affect data roaming...
1. Your PRL. Call up *2 and tell the friendly rep that you would like to be flagged for a PRL update. 90% of reps will do this no problem. If you get one that won't, hang up and call back.
After you get flagged, wait a minute or two, then call *2 again--you should get redirected automatically to an automated PRL updater, which updates your PRL over the air while you're on the phone. It's all automated.
The latest PRL is 20229.
2. If you still can't data roam after that you might need a PRI (confusing I know) update. Go to Start->Settings->System tab->Device Information and report what your current PRI version is.
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