Did you lower your minute rate plan at some point? How much you are paying AT&T will partially determine when you can do an upgrade. So if you are on a minimum rate plan, expect to have to wait 21 months. If you have unlimited minutes, you can do one almost every year. And it's an Apple stipulation that they can't do an early upgrade for iPhones, unless you pay the extra $200 (or for no contract, you would have had to pay $599 or $699 for the 3GS). And yeah, all of the carriers are about the same as far as customer service goes. These companies are so huge that the odds of having a problem at some point are pretty good, and there's plenty of inept people who are employees (about the same ratio as the real world I'd say ). I recommend finding a rep at a store who seems to know what they're talking about and is straight with you. Take their business card, and make them your personal connection with AT&T, or whoever. Keep going to that same person for all of your business, whether it's buying something or just getting information, and it'll significantly decrease the chances of running into something like this.