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Going from the X to the XS Max. It was just a bigger X and it was at that point I realized I didn’t want the plus sized phone any more. I went back to regular size when the 11 came out. Unfortunately it sounds like I might have to get a plus sized phone again this year for the better camera according to the iPhone 15 rumours
 
The 8+. I should have just kept the 7+, cause it was practically the same and less buggy. Other than the 8+, I never regretted an iPhone purchase.
 
The 8+. I should have just kept the 7+, cause it was practically the same and less buggy. Other than the 8+, I never regretted an iPhone purchase.

Interesting you found the 8+ buggy. My 8+ was perhaps the most solid iPhone I’ve owned to date apart from my current 13 Pro Max. It’s probably the one iPhone I look back fondly at as it was just so reliable.
 
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My 1st one (the 5). Because after that, I just wanted more and more of them. I now have the last of the Minis (12) and while I don't regret getting it, it's kinda sad knowing my next iPhone will have to be the size of a tablet and won't fit in my pocket anymore. I will also need both hands to use it.
 
Interesting you found the 8+ buggy. My 8+ was perhaps the most solid iPhone I’ve owned to date apart from my current 13 Pro Max. It’s probably the one iPhone I look back fondly at as it was just so reliable.

And the ironic thing was I bought it cause the design and touch ID was proven. I wasn't ready to take the chance on the X design. But the 8+ didn't treat me well.
 
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Interesting you found the 8+ buggy. My 8+ was perhaps the most solid iPhone I’ve owned to date apart from my current 13 Pro Max. It’s probably the one iPhone I look back fondly at as it was just so reliable.

I agree with this. Absolutely same experience. Although my 11 Pro was a champ as well.
 
The iPhone XS nothing but issues with hardware and my first one was replaced by Apple due to a hardware issue on the logic board. Second one had the same issue and instead of accepting a third XS I paid a little extra and got my 11 Pro.
 
Let's be real. There are times when serial upgraders regret getting a particular iPhone that year. For me, it was the iPhone 7. I was coming from the SE1 after using it for a few months. The battery life was solid and the small form factor was still an appeal back then. When the 7 came out, I obviously have to have one. And when I did, I was disappointed with how "cheap" the word "iPhone" look at the back of the Black version. The battery life on the regular 7 was straight up below average too. All in all, it was a subpar experience and the 8 fixed the gripes I had with the 7.

What is yours
The 7+.
Upgraded from the 6, a family member was needing a "new" phone so I upgraded to the 7+. Went with the + so therew as a noticeable difference between models. I didn't like the bigger size.

The "worst" phone is a different case. My first, the 3G, had no headroom for future OS and apps improvements. From the era when Apple still didn't know if they would succeed in phones, so don't overengineer.
 
definitely the 14 pro max for me right now

the 13pm might have been one of my favorite iPhones of all time. amazing battery life, the screen upgrade from the 12pm was night and day (12 had the yellowish screen cast, and no 120hz). in meaningful ways it felt like a nice upgrade from the 12 series

the 14pm does not feel meaningful. dynamic island was super clever when I saw the keynote but in use it's a mild quality of life improvement. the photos from the phone are not a noticeable upgrade as I rarely use the pro raw mode. and superficially I prefer the phone colors on the 13 series - the graphite and alpine green I like better than space black and deep purple.

plus subjectively my opinion is shaped by the fact that I had purchased a basically brand new green 13pm for a deep discount second hand on Facebook marketplace, so it makes it feel even more like I had no need to upgrade and had a perfectly fine phone.

all that being said I do like the 14pm and of the iPhone lineup this year this is the phone and color that I would upgrade if I actually needed the upgrade. but if I could go back I'd just hold onto the 13pm another year
Why would you upgrade to 14 pro max, if you got the green iPhone 13 pro max that came out mid cycle which means you barely had the phone for long. I agree the alpine green colour to me is a better colour than the 14 pro line up. You need to at least keep an iPhone for a year to get any use out of it.
 
The 8. I preordered as I was on a two year cadence at the time (coming from a 6S).
Should’ve spent the extra cash and bought the X. Such a leap forward!

Most satisfying upgrade was going from the 4 -> 5S (tied with the 3G -> 4). Loved my 5S (still have it).
 
Why would you upgrade to 14 pro max, if you got the green iPhone 13 pro max that came out mid cycle which means you barely had the phone for long. I agree the alpine green colour to me is a better colour than the 14 pro line up. You need to at least keep an iPhone for a year to get any use out of it.
Yeah it didn’t make sense. I spent parts of last year bouncing between the mini and the max, hence the mid cycle switch.

And I’m a perennial upgrader also, which is why I went for the 14 pro max.

Most years it’s a nice treat to get the latest and greatest and justified in my mind as it’s my most used personal piece of technology.

But as I said this year more than most felt like a side grade
 
iPhone 6 Plus

It was a slow, underpowered disaster with 1GB of RAM and a high resolution screen.

The battery was a disaster that would shut the phone off randomly at 10-30%. Then secretly they added the speed throttling to avoid that which made the phone even slower.

An absolute disaster of a “flagship” product.
 
iPhone 7 too. Nothing special. Poor battery. It was not equipped with telephoto camera. Absolutely an useless upgrade from iPhone 6/6s.
 
Yeah it didn’t make sense. I spent parts of last year bouncing between the mini and the max, hence the mid cycle switch.

And I’m a perennial upgrader also, which is why I went for the 14 pro max.

Most years it’s a nice treat to get the latest and greatest and justified in my mind as it’s my most used personal piece of technology.

But as I said this year more than most felt like a side grade

I’d get bored of phones very quickly if I was upgrading every 12 months. I have to see a difference personally, otherwise it seems like a waste of money for me. It all feels like a bit of a con now these phones have gone stupidly expensive and barely anything changes now the technology has matured.
 
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Interesting you found the 8+ buggy. My 8+ was perhaps the most solid iPhone I’ve owned to date apart from my current 13 Pro Max. It’s probably the one iPhone I look back fondly at as it was just so reliable.

That's also something I find a bit surprising as I have heard more wrong with both the 6 and 7 series than anything 8 related.
 
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it all depends on which phone you are coming from. Like for eg majority coming from 6s plus to 7 plus might feel 7 plus is waste but f you are coming from 6 plus to a 7 plus you will see major differences.

But i guess in general 7 series /xs series will see big voting for regrets followed by 11/12
 
I would say mine would be iPhone 4 and iPhone 12 - my 4 was riddled with software & hardware issues and iPhone 12 didn’t impress me with 5G speeds & battery life.
 
I would say mine would be iPhone 4 and iPhone 12 - my 4 was riddled with software & hardware issues and iPhone 12 didn’t impress me with 5G speeds & battery life.

My 12 mini, which is my favourite iPhone to date got just over 500Mbps on 5G, in South Africa. Problem with that was I burned through 1GB in 3 seconds flat running Speedtest. I was on pre-paid. I now keep my phone only on LTE/4G, and I don’t run speedtests on mobile data anymore.
 
Mine was the 12s. The 12 pro and 12 mini, sub par battery really sucked.

I suppose that depends on what you need the phone to do. My 12 mini often goes the whole day, and then some, mostly just playing music through BT headphones, in other words minimal screentime, unless I’m taking lots of photos/video, navigating with GPS in the car, hotspotting, launching actual rockets in to outer space etc.

I suppose the removal of the mute switch and SIM tray on future iPhones is going to allow for a monumental bigger battery….
 
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iPhone SE 1st Gen. Not having image stabilization when recording video was a huge turn off.
 
iPhone SE 1st Gen. Not having image stabilization when recording video was a huge turn off.

Ok, that was the phone I actually regretted getting, for that reason, and the battery. 100 times worse than the 12 mini. My 1st gen SE can barely still play Apple Music, if I can even get the thing to boot. Battery is completely finished now, and even plugged in it keeps on spantaneously restarting. I’m literally using it as a paper weight now. Barely got 5 years use out of it. On the other hand, my 2011 MBP is still somewhat useable, battery now over 2000 cycles, the only real reason I got a MBA M1 was because of software compatibilty.
 
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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.
 
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