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well let me tell you, that same hole was in at&t's system back when the 3G came out. and i was able to order multiple phones with the subsidized price, so i'll take my chances :D
There is no hole. Sounds like a simple & rare mistake that you experienced. It's not happening these days.
 
So I'll buy a new iPhone 4 for my second line at the early upgrade price ($399), then activate it with my main line.
This will work, right?

I just won't be able to upgrade either lines again for another 2 years.
 
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