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It's entirely up to you, and your needs/wants in a phone. Some folks do it yearly, others have 5 generations old phones. There's no right or wrong answer. Usually from one year to the next, the improvements can be minimal, I'm on an upgrade plan, so usually I upgrade each year. But that's just me, I get bored easily.
 
How much do you use your phone? I find people who upgrade their phones often are heavy users of their phones (though this is heavily dependent on available funds). There are a lot of college students I know who are still using iPhone 6s heavily even today.

I upgrade every year with the Apple Upgrade Plan - though I'm planning on going back to a 2-3 year upgrade cycle (been saying that for years tho).
 
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Each to his own desire and pocketbook. I love learning new technologies. Phones, PCs, TVs, Routers, Modems etc etc etc. keeps my mind active.
 
Every year or every two or three years? I currently own iPhone XS Max
We upgrade every 2.5 to 4.5 years and usually use our tax refund to pay the down. Before Android last year we did 4.5 years with our 6s and 6s+.

My 6s+ still has an active SIM and gets used regularly as a backup phone.

I suppose the answer is 'whenever you're ready'.
 
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I've personally moved to a 3-4 year upgrade schedule (used to be every 1-2 years or less). With how minimally phones are changing with each iteration, it just seems like a waste of money and effort to get some nice updates that likely will change my phone usage experience very minimally.

I'm also using an XS Max (got it on release day) and either am going to upgrade to the 2021 or 2022 iPhones most likely. The only reason I'm considering upgrading this year is mainly due to 5G and the improved reception of the Qualcomm modem. Otherwise, my XS Max is basically running as great as it was on day 1, and I really don't know what I'd get by upgrading.

I even used to be the one to say that having a ProMotion display on the iPhone would get me to upgrade, but now I'm not sure that even would motivate me to spend an extra $200-300 for the Pro models over the regular/mini models when I upgrade (assuming only the Pro models get the ProMotion displays).

My mindset has definitely shifted a lot from what it used to be. I guess my priorities have changed.
 
Every year or every two or three years? I currently own iPhone XS Max
Only you can answer that question, use to upgrade yearly, now it’s every 2 years, went from a perfectly working xs max to a 12 pro max, wanted that awesome best in the business battery life and camera features, in saying that though the xs max is still a awesome phone.
 
I’m guilty of upgrading whenever the mood strikes me. That said I made it just under a year with my last phone before I bought this SE2020. I’m going to try to keep this phone till AppleCare runs out or the phone doesn’t support security updates. Whichever comes first.
 
Until my 8 I was caught up in the 2 year replacement cycle that followed the old skool phone plans that subsidized the cost of the hardware. With my last phone I bought it outright and am going to sit on it until it becomes unusable, camera upgrades are useless for me and I really don't rely on my phone for more than talk, text, maps and email viewing.
 
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Every year or every two or three years? I currently own iPhone XS Max
I also have a XS Max, my first iPhone was a 6+, but I got it the year after it came out, well about 6 months later, so when the 6S+ came out I got that, next year I got the 7+, didn't like the 8+ or X, but when they released the XS & XS Max, I jumped at the max, so it was every year, but I would pay them off, so I owned them, so if the new 2021 iPhone has 1TB, I'll be buying that, and hold onto it for 3yrs like the XS Max will be 3yrs in September.
 
I’m guilty of upgrading whenever the mood strikes me. That said I made it just under a year with my last phone before I bought this SE2020. I’m going to try to keep this phone till AppleCare runs out or the phone doesn’t support security updates. Whichever comes first.

So....when AppleCare runs out then.
 
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AppleCare can now be a monthly subscription that can continue on as long as Apple supports the phone.

I know but if the commenter was on monthly plan, it wouldn’t end. Based in the commenter saying the earlier of the two, that’s only possible if it was the 2 year (however many years) plan, not the monthly.
 
I pay the monthly fee for AppleCare. Not sure how long it’s supported that way

Ah. So then it’s whenever you choose to upgrade not the earlier to the two options you listed, since one ends when you decide it ends. They’ll take your money for AppleCare as long as you’re willing to pay it. Unless it was the 2 year plan they you spread out over 24 months that you can do with the Apple Card (not sure about other forms of payment).
 
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