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Iphone 14 Pro max i'd have to say. It's not like theres anything wrong with it, I came from a perfectly working 12 pro max so it was a completely unneeded upgrade, still not sure why I did it. Usually keep phones for 3-4 years.

If you’re into phone photography then you’d see the difference.
 
4S. I was coming from a 4, and while Siri was new and interesting at the time, the novelty wore off in a day or two and I was stuck on two-year contract with at&t for a phone that wasn't any different than my 4, and I couldn't jailbreak it.

It's probably one of the main reasons why I've never purchased a phone from a carrier since, and just pay full price upfront directly with Apple. I haven't cared about jailbreaking iphones for years.
 
I have not regretted buying any of my iPhones. I've regretted some iOS updates, but the next one usually followed quickly and sorted out whatever caused the regret.
 
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