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I guess we'll know for sure tomorrow when I try to place an order for 2 iPhones on Apple's site. We are on the Family Plan and both have 3G's, two lines. Should be straightforward since it says existing AT&T customers are eligible to purchase the upgrade one per line.
 
I do not think that is fair if you have to go into the store, especially if Apple will not allow authorizes users buy the phone. I am on a family plan with my husband, and we both want to upgrade. The account is not in either of our names due to it being an old account and just not wanting to go through the hassle of changing it. We live in the same household as my mom, whom also wants to upgrade. She is on her own family plan with my dad and brother.

They seriously cannot deny all of us phones.
 
I just did an apple store chat and the woman said I would be able to order both phones on the same order tomorrow from apple's website. She also said there was still no word on when preorders start.

I just chatted to an online Apple Store representative who told me that family plans can only upgrade their phones in store. (AT&T stores)

My girlfriend and I walked into the SoHo store to upgrade our original iPhones to 3Gs, and it was fine.

This time I want to pre order and get the phones delivered but no one seems to have a definite answer?

It seems these reps are giving conflicting info. What's the real story? I'm in this exact situation and would prefer to order both phones from Apple.

Would AT&T purposely give false info to drive traffic to their stores?
 
I have a family plan with 4 lines and when the 3GS came out I preordered 4 iPhones... had them all delivered and they all got there on launch day. I see no reason why Apple or AT&T would stop doing that for this release, especially when they did it last year.
 
did you place 2 orders or were they both on one transaction/credit card?

Although the pre-order rules may differ, the following test may be telling:

I just tried to upgrade two phones on our family plan (for the 3GS) on apple.com. I was able to place both phones in the cart, but was not allowed to proceed with the purchase. I received a message advising me to remove one phone or save it for later purchase. This seems to corroborate the one phone per order experience of another member. I expect to be able to place the orders separately without any problem.
 
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