All Things Apple

Recently, I made a major logistical decision to switch completely from Windows to macOS. I had been running Bootcamp for many years on MacBook Pro laptops, and almost exclusively booting into Windows.

OK, wait. Why would I do such a silly thing?

It all started decades ago, when I became a diehard IBM ThinkPad fanboy. The devices were solid and reliable, without superfluous bells and whistles, and just got the job done. They usually lasted a few years before the specs just weren’t good enough. It wasn’t necessarily because of hardware failures or flimsy construction that I needed to upgrade.

Then IBM sold their personal computer division to Lenovo. They kept on the ThinkPad tradition, but over the years, the quality started to dip, and the unnecessary extras started piling on — whether it was quirky hardware options, or tag-along software packages ala Dell. I started getting frustrated.

Then, I decided to jump hardware ships to Apple, and never looked back. Although extremely marked up in price (the “Apple Tax”), they were just built well. Aluminum chassis. Reliable keyboard. They just worked, well above par from similar makes and models. (I am not claiming they were or are perfect — just that the standard was better and they felt more robust.) I started with Bootcamp from day one. I never even tried Parallels. I booted into macOS only seldom, as there was almost never a pressing need.

A couple things happened in the most recent past. First, Apple has abandoned Intel CPUs for their own silicon. That means that Bootcamp is out of the question for future models, and I knew I was getting close to needing a hardware upgrade after a few years with my current MacBook Pro.

Next, my son stopped playing Fortnite, which we would occasionally enjoy together, and hence I stopped as well. So I didn’t need a gaming experience anymore. Gaming on macOS is lackluster and sparse, but that is irrelevant if you’re not even gaming at all.

So, with a pending M1 or M2 chip in my destiny, I decided it was time to abandon Windows completely, and go all-in with macOS. It took me around two months to fully embrace the decision. The execution was painful and took a few weeks. Now the dust has settled, and I’m actually really pleased. The hardest part was finding a suitable replacement for Quicken for Windows, which I use to keep track of our home finances. I settled eventually on Banktivity, and it’s working well for me. So I’m a happy Apple geek.


After the switch, and spurred on because of the switch itself, I got totally screwed by Apple on a major UX failure. I do bear some minimum of responsibility, but nonetheless, I firmly believe it’s mostly a mistake on Apple’s part.

I have for years had two SIM cards — one for Denmark, and one for the US. And whenever I’ve upgraded my iPhone, I’ve kept a defunct phone sitting at home with my AT&T SIM card, set to auto-forward calls to voicemail so I don’t get dinged by international calling rates. This way I could still get regular SMS messages to my US number. I was delighted when I could auto-forward these messages to my main iPhone. Huzzah! I was able to get my messages all in one place.

Then All Awesome Things Apple took it up a notch. Once I started using macOS daily, I saw that I was also getting iMessage and SMS texts directly on my computer. I actually found this to be completely fantastic.

At one point, my old phone, with the AT&T SIM card, started complaining about space problems. I went into Settings on the phone and looked at Storage, and could see that my Messages app was eating up over 3 GB of space. “Huh,” I thought. “I don’t really need to keep all these messages on this old phone. I can just keep them only on my new phone, and on macOS.”

So I flipped the switch for “Message History” from “Keep Messages Forever” to “Keep Messages for 30 Days“. And Dumb Me presumed (wrongly) that this setting was local to my phone. Not global to my entire iCloud account.

I never got any warning message on the old phone to the tune of, “Hey, are you sure about that? You’re about to remove 3 GB of message history that we know you have meticulously backed up for more than a decade, because you like to be able to see old messages with your family and friends. You like to peruse photos and videos and sound clips you have joyously exchanged with people you care about. Oh, and perhaps more importantly, this is a global setting, which means that all those messages will also POOF disappear on your other iPhone and your MacBook, and even a Cloud-based backup of your phone will not restore them. They will be wiped from existence. Are you really, really sure you want to make this change?”

No, there was no warning. Just a silent deletion of all my messages. I first noticed around a week later. It was too late.

And a week before that, I had purged some old iPhone backups on my disk, because they were on the Windows partition, and I just didn’t think I would care about them ever again. Joke’s on me!

Should I have thought twice before making that change to the settings in my old iPhone 5s? Yes. Do I think it’s a massive UX failure by Apple? Yes. I was on the phone with them in Ireland for like 45 minutes complaining about this. I’m hoping Apple considers some UI changes in the Messages Settings to at least warn users that the “Message History” setting is iCloud global — if you are using iCloud-based Messages, that is. That was also something I had recently changed. “Might as well back that up in the cloud too, right?” I would have been better off never backing it up in iCloud. But I just didn’t really know.

Anyway, <rant off>. I’m still overwhelmingly pleased with transitioning from Windows to Mac. I’m not gaming at all anyway, and I’ve adjusted fine to using Mail instead of Thunderbird (it was too buggy for me on macOS with multiple IMAP accounts). And I love having a real shell terminal. In general, the fairly seamless integration between and among apps and devices in the Apple Universe is well-executed, whereas it always feels like a kludgy add-on for Windows.

If you need emotional support to make the change, feel free to reach out. 🙂

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