Moving Back to Microsoft Windows – Unexpectedly

This isn’t what I expected to be doing over the past five days: setting up a new laptop and especially, returning to the Microsoft Windows ecosystem. When I left Windows last time, I never thought I would return to it. I left Microsoft in 2017 and you can read more about it here and here.

What changed?

On Friday afternoon, my two-year-old M1 MacBook Air started acting wonky (yes, that is a technical term). After extensive research, attempting to resurrect it without success, and then finding an article which described exactly what was going on, and ended with the dreaded words – go to your local Apple store to either have a new motherboard installed and/or be ready to buy a new computer.

Over the years, I haven’t had too much luck with Macs (I’ve had three), though I still have my 2017 iPad Pro (with battery life issues) and I love my iPhone 12 Mini. While I love Macs when they work, it seems that the way that I use, err abuse a laptop doesn’t lead to long lived machines and I usually get is 2, maybe 3 years.

With my history of destroying laptops, my wife isn’t a fan of the Apple tax you pay each time you buy an Apple device and indicated if I wanted a new laptop, I should look beyond a MacBook. At that point, I was frustrated and agreed that it was probably a great idea.

Thankfully, I had a good idea of what was out there for Windows laptops since I found one for my stepdaughter last fall and quickly found a similar one in stock locally. She hasn’t had any issues with it and is happy with how it works for her. They also had in stock MacBook Airs and Pros, so if I decided to bear the cost of staying with Apple and the ire of the wife. I could get one.

When I got to the store after supper and looked at their in-stock options. I was very tempted while looking at those new Macbooks and how easy it would be to simply log back in and have everything work. The more I thought about it, the Apple tax was more than I was willing to deal with both price-wise and wife-wise.

The one I looked at online best met my needs, and price point.

Yes, I had decided to move back to Windows.

I knew that by switching back to Windows I do some head scratching, wondering WTF I switched, and a little swearing, but I figured that it wouldn’t be that bad. Especially, since I’ve been using Windows since version 1.0, and even though I went with Apple over past few years, I have kept semi-current with what’s going on in Windows, because I still take care of my wife’s Lenovo.

So, I walked out of the store with an HP Envy x360 for a decent price.

Growing Pains

Even so, I knew there would be growing pains, but I was also confident in my ability to minimize or at least figure things out.

Surprisingly, what I found to be the hardest part of moving back to Windows this time was…the choice to move away from Apple, Google, and other vendors as much as possible (though I stuck with Reflect Notes) and go all-in with Microsoft. You don’t realize how many sites or programs you must change once you make that kind of commitment—it was more than I initially thought it would be.

Although there a few things that haven’t changed that much since 2017, but as long as I can still find the correct checkboxes that are hidden behind the veil, I think I can deal with the worst of Microsoft’s intrusions.

Everything was going well (just time-consuming) until Outlook (one of my least favorite programs of all time) started putting all of my emails into the Deleted Items folder. I fiddled around for over three days attempting to correct that issue. I got quite frustrated and seriously thought about using a different email client. Finally, after reading too many contradictory online articles, chat histories, changing settings, running deep security scans, and deleting/reinstalling apps,

I figured out what the problem was: I had hundreds of legacy Hotmail and Outlook filters still active in Outlook, and somewhere in that gaggle of filters was one that was messing up the entire system.

Once that aha moment came about, I had a choice – go through hundreds of filters to hopefully find the one causing the issue or delete them all and start over. I quickly decided to delete all my email filters, and guess what–I started getting email in the Inbox. Problem solved. I know I will have to start over filtering emails again, but at least this time they will be current.

The reality is that

I did not anticipate this move back into the Microsoft tech silo being as much work as it turned out to be. Plus, attempting to setup my iPad Pro and iPhone into Microsoft-compatible devices at the same time only contributed to my growing frustration levels.

However, I’d say I’ve gotten things to about 80% and can start getting into a good routine with this new setup. Though Loop does intrigue me (similar to Notion), and I will be tinkering with that over the next few weeks to see if it something that I want/need to add in or leave alone.

Now that I’ve got things semi-under control, I’m not second-guessing making the move, though I was beginning to wonder on that third day of the Outlook fiasco a little. My HP is now running smoothly and doing almost everything that I want.

The biggest thing that I am missing is the ability to receive and text from the computer, but Microsoft is working on that and will at some point (this year?) have a functioning Phone Link app that will let me do that. I just hate typing on the phone, but I still have my iPad Pro and its keyboard to use as a work-around when I need to.

These things happen for a reason; I just have to figure out what the reason was this time.

Maybe the good thing about all this work I did with the email fiasco and switching back to Microsoft, is that I had to go through all my settings, do a complete security check-up on all my accounts, delete crapware, learn a little about the intricacies of Windows 11, change a bunch of passwords, and get rid of a bunch of old internet accounts that I no longer use.

It sounds almost reasonable. 😊

Now to remember that I have a delete key and Ctrl-backspace is not delete. One of those muscle memory things that is catching me too often, but I will adapt.

Back in the world of Microsoft, let’s see how it goes this time.


  1. You’re brave man!
    Just moving from one PC to another can cause problems. It does take skill and some patience and I would not want to move between OSs.


    • Thanks Andy – Getting a new computer wasn’t what I wanted to do, but I’m on one so much that the wife didn’t complain about me getting a new one when the MacBook Air stopped working. She just has a problem with the Apple Tax. Moving back to Windows was unexpected, but now that I’m mostly done, some things do work better for me than they did with the Macs. Just another part of the adventure. 🙂 Good luck on Monday and I’m sure you’ll do great!

      Liked by 1 person

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