Upgrading phones is a bad experience
2024/09/24 #uiuxI upgraded my phone last Friday, swapping my beloved purple iPhone 12 mini for a new iPhone 16 Pro (in the much more boring natural titanium color). Generally, I always try to skip a few phone generations and "only" buy a new one every 3 to 4 years or so (and I won't go into the story how the life of my iPhone X tragically got cut short by an accidental rollercoaster ride in the washing machine today...).

Another reason not to upgrade too often
There are several reasons why I rock my phones for at least 3 to 4 years before ditching them for the newest shiny hotness. Being mindful of earth's limited resources is one, saving some money along the way is another. But to be honest, both of those got surpassed by a much better reason that I was forced to (re)discover on Friday: avoiding the awful experience of transferring my old phone to the new one!
Switching phones sucks
The honest truth is: switching (i)phones sucks! I don't know if it didn't suck as bad last time or if I just forgot about the last time because it was 4 years ago but whatever the case may be, it's bad. I consider myself pretty educated when it comes to this sort of stuff so I knew what different methods there are to transfer your data from one iPhone to another. I opted for device to device transfer using the "Quick Start" function and it still took me the better part of a weekend to get to a state where I can leave my old phone at home when I go outside and still have everything I need available to me on the new phone. As I am writing this post I am still waiting for two apps to stop freezing on launch though.

Why it sucks
Let me list the things that sucked about the whole process (I am aware that every user has a different experience switching phones so I am happy for you if you didn't run into some or any of these issues yourself but please respect that these were the ones I myself encountered):
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Inconsistent experiences without feedback: When I first tried the device to device-transfer it said that it will take 2 hours. I knew something wasn't right with that number because my wife's phones just finished the same process in 15 minutes earlier. After waiting for a while I restarted the process (which was a pain in and of itself) and it then completed the whole thing in under 20 minutes.
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Premature prompt to erase my old phone: Right after the transfer was done the setup wizard asks you if you want to erase your old phone. This is very much premature as many things do in fact not carry over to your new phone and erasing the old phone at this point could have costed me many hours on the phone with various banks to get my new device approved again.
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Painful process to make sure every app works again: As mentioned in the previous point I had to make sure all of the apps (banking apps, authenticators, the ID apps, etc.) that used my old phone as a device verification method also accepted my new phone. For none of these apps this was done automatically and transferring this to a new device was handled differently by each of them. This took several hours and some of it couldn't even be completed until 24h later due to the security requirements of some of those banks/apps.
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Lack of communication: Since I currently live in Hong Kong and bought my new iPhone 16 Pro here I was not able to transfer my e-SIMs to my new device (iPhones sold in mainland China, Macao and HK do have two physical SIM slots instead. At no point during the transfer or setup process did iOS communicate this or how to deal with this at all.
- Random settings changes: When I was finally done with most of the manual work required to get my new iPhone up to speed I realized that several notification settings had changed (or rather enabled themselves) for some reason. This is most likely just a bug and not some nefarious practice by Apple but it is annoying nevertheless. Marco Arment mentioned something similar happen to him regarding the Apple Sports app on Mastodon.
Why not make it suck less?
If the experience of switching from your old phone to a new one sucks so much that it could actually make some people (like me) hold out buying a new one for as long as possible you would think that smartphone manufacturers (and/or smartphone OS manufacturers) would do everything in their power to make this process as frictionless and enjoyable as possible.
There are of course apps from both Apple and Google to facilitate switching from iOS to Android and vice versa. Providing tools like this is table stakes and mostly aimed at combatting platform lock-in. As my most recent four phones have all been iPhones I can't and won't say anything about how well these work and how smooth of an experience switching from Android to iOS or the other way round actually is.
But what I don't get is why the experience of switching from old iPhone to new iPhone – a user experience that is almost entirely in the hands (and financial interest) of one company (Apple) – is so horrible. I mean, just look at Apple's official documentation on "Moving to a New iPhone or iPad". It's a mess even if it all ends up working as advertised without any hick-ups in some cases.
A complex problem to solve
I'm left with two conclusions: First, solving this problem is in the clear interest of all smartphone and smartphone OS manufacturers as it probably deters a significant amount of users from upgrading more often. Second, the fact that this problem is not solved yet (despite of the first observation!) leads me to believe that this is a complex issue that might not be so easy to solve after all.
To me, it comes down to making an effort to tackle all of these small issues which add up to create this mess one by one. There's not a simple solutions, but a lot of small steps to a better, more consistent and more enjoyable experience. I just hope it has gotten much better next time I have to upgrade my phone. That will give you another 4 years, Apple. I hope you use them wisely!