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This is not true, at least in my case.

My 2yr/unlimited contract technically ends 9/23/2015, yet AT&T reports that I am now eligible for upgrade.

Perhaps it's because my contract ends in September, rather than your October?

You might want to check further into your account. My contract date is 10/01/2015, and AT&T says I'm now eligible for an upgrade. However, when I click to see my upgrade options, I'm only eligible for a Next upgrade and I "may be eligible" for a 2-year contract upgrade on 10/01. Going to contact them today to try to get that date bumped so I can do the pre-order on Saturday.
 
FYI my you can also preorder using the Apple Lease. I spoke to customer care this morning. They are treating Apple Lease ph New like BYOD phones. Buying a phone from Apple directly will have no affect on your contract.
So preorder from Apple using the lease program on Sept. Pick up phone on Sept 25. Order another iPhone 6S from online ATT when eligible, sell on EBay. Profit!
 
I've never ordered from the AT&T site before but I heard last year that during the process AT&T didn't offer an option to keep an old plan (like unlimited data) during the ordering process -- but forced you to select a capped plan. Apparently, the instructions from customer service was to select a new plan, then call AT&T and they'd put the unlimited plan back on. The problem was, when people called back to get their unlimited, the operator didn't know what they were talking about and refused.

I don't have first hand knowledge if this was actually the case, but I did see lengthy threads last year from frustrated AT&T customers stating as much. I'm almost tempted to pay full price to avoid any hassle.
 
I've never ordered from the AT&T site before but I heard last year that during the process AT&T didn't offer an option to keep an old plan (like unlimited data) during the ordering process -- but forced you to select a capped plan. Apparently, the instructions from customer service was to select a new plan, then call AT&T and they'd put the unlimited plan back on. The problem was, when people called back to get their unlimited, the operator didn't know what they were talking about and refused.

I don't have first hand knowledge if this was actually the case, but I did see lengthy threads last year from frustrated AT&T customers stating as much. I'm almost tempted to pay full price to avoid any hassle.

No hassle at all. Your current UDP will appear as an option during the upgrade process. If you have patience and perseverance, you'll survive the crush on AT&T website.
 
I've never ordered from the AT&T site before but I heard last year that during the process AT&T didn't offer an option to keep an old plan (like unlimited data) during the ordering process -- but forced you to select a capped plan. Apparently, the instructions from customer service was to select a new plan, then call AT&T and they'd put the unlimited plan back on. The problem was, when people called back to get their unlimited, the operator didn't know what they were talking about and refused.

I don't have first hand knowledge if this was actually the case, but I did see lengthy threads last year from frustrated AT&T customers stating as much. I'm almost tempted to pay full price to avoid any hassle.

I have done that for the past few years and I haven't had any issue with getting my unlimited data back after calling. I just did it again last year for the iPhone 6.
 
Has anyone been able to get their 2 year contract eligibility date changed to take part in the pre-order? I've already tried three times now with no luck. One of the reps even changed when my contract expired, but it had no effect on the upgrade eligibility which seems bizarre. The second rep I spoke to claimed the contract has nothing to with upgrade eligibility, which I find hard to believe. AT&T really seems to be making it difficult for existing customers to buy a subsized phone with a contract and instead keep insisting I go with Next.
 
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