Apple – the problem of syncing the iPhone

Once upon a time Apple created hard- and software solutions which where sleek and user friendly – no more! Syncing is a joke.

From a standpoint of 2022: The iPhone has been one of Apple´s biggest success stories and introduced the “smartphone” to the world when everybody was still typing away on their little Blackberry keyboards and ticking checkboxes on their Palm PDAs. Apple sold Steve Job´s brainchild since its introduction on January 9, 2007 more than 2,2 BILLION times (as of November 1, 2018), in numbers You might presume, that means there is ample support for the product, right? Nope.

“The iPhone is one of the two largest smartphone platforms in the world alongside Android, forming a large part of the luxury market. The iPhone has generated large profits for Apple, making it one of the world’s most valuable publicly traded companies. The first-generation iPhone was described as “revolutionary” and a “game-changer” for the mobile phone industry and subsequent models have also garnered praise. The iPhone has been credited with popularizing the smartphone and slate form factor, and with creating a large market for smartphone apps, or “app economy“. As of January 2017, Apple’s App Store contained more than 2.2 million applications for the iPhone.” from Wikipedia

If one wanted to keep his data as a backup or sync with a new generation iPhone, Apple provided a service within iTunes which did the job – fairly well. In the beginning. The bigger the Phones hard drives got, the more photos one shot, the more Apps one downloaded, the bigger these bloated backups got. Space on a hard drive and specially on SSDs does not come cheap, but for your most important data, at hand every day – your contacts, notes, emails, Chat Apps and photos – there must be a reliable solution, right? For that enormous amount of customers a single question may be crucial: in the case you lose your phone, get a new one or it gets stolen,…how did you get your data to a new device or browse the contents independently?

Well, iTunes was the first answer for years – but then syncing became patchy and problematic, specially with older macOS versions vs. newer iOS versions. Power user do not tend to always adapt to the latest Apple OS updates, now coming in every year, and syncing became a hazardous game, either working or not. Even mounting an iPhone on a certain Mac became a tedious task, often it looked like erratic luck. What of all of that in 2022? I needed to sync the data of an iPhone7 to a new iPhone13 after 4 years of heavy use…and I ran into several hard walls or problems to overcome.

PROBLEM 01 – iTunes

Well, Apple simply DISCONTINUED the use of iTUNES as a syncing Hub. WTF?! My Camera Roll was not synced for ages. macOS Catalina will do now the job from the Finder (they promised), as Apple decided to break up iTunes for Mac into smaller programs. I see. Thank you Apple to have not thought of this beforehand and make our one-stop-shop for media into a horde of little booths. And Catalina? Well, you need to have this OS at hand, as still a lot of us are stuck in Mojave. Well, Catalina it is, ok…BUT:

PROBLEM 02 – Syncing with Desktop/macOS Catalina

To backup a Phone which did not get backed up for a while, a certain error kept appearing. It starts fine, sees the iPhone7 and then runs into: 

PROBLEM 03 – There are purchased items on the iPhone…

I kept getting the Error: “There are purchased items on the iPhone…”. And it did not go away, no matter what I tried. So I consulted th Apple Support Forums, where I found a hint from “megarecommended” (Apple recommended this third party opinion with a badge including their famous apple symbol) user turingtest2 who says:

See Hide and unhide music, movies, TV shows, audiobooks, and books – Apple Support and Redownload apps, music, movies, TV shows, and books from the App Store, iTunes Store, and Apple Books – Apple Support.

The latter leads to a beautiful:

“The page you’re looking for can’t be found.” What!?

Beautiful. Really?!

At the latest here Apple lost me. Sorry. Strict no-go.

The user turingtest2 or tt2 (his short form) has Level 10 (244,905 points!) in the Apple Support forum. So what can possibly go wrong with a  technical hint from 2019? It does not exist anymore? Apple, where are thou…?

I like tt2 – in 2018 he wrote (concerning the same problem) – do very much think:

“It would be nice if iTunes could be a little less cryptic. 😕”

It is outrageous for a big company to create such one way streets and drop support like this for a major product? Syncing across multiple devisces is a landmark pillar of Apple quality. It´s seems like madness or they gathered a greedy virus from Microsoft, I presume… 😉

SOLUTION – and no endorsement

So I looked around to find a third-party solution and there are several. That I did have to use a free third party software to secure my data, including the voice memos and books, is a real shame for Apple. A real shame. Make your own inquiries. They jumped in and bridged the gap, but these solutions are costly (30-50EUR) and likely develop into a costly yearly subscription funnel in the end, ripping off unfortunate users who are in desperate need of a solution to save their data. You bump into advertising articles like this, quickly…

AnyTrans ( did it for me in the end, no endorsement – I also checked first if the App is real and not full of spyware (like the infamous MacCleaner), but seems to be legit, given the wide range of reviews. It did the job which Apple quit to d, but I found myself in a situation to pay for a service of a multinational with luxury communication products which was once free and stable.

Not a good development and a very bad and foretelling road we seem to be all on…

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