The Business of Software

To Microsoft: Kudos on the Windows 10 upgrade experience

Upgrading to Windows 10 went flawlessly. This isn’t the same old Microsoft.

By Jim Grey (about)

I’m a Windows user. I see how all the cool developers have switched to Mac. I was a Mac user once, so long ago that MacOS was still called just System, and it was on version 6. Work demands switched me to Windows before System 7 came out, and I’ve just stayed with it.

And until recently I’ve never upgraded from whatever version of Windows shipped with my PC. But I bought a cheap Windows 8 laptop a few years ago to schlep to the coffee shop to check email and write in my blog, and I found the “tile world” Windows 8 UI to be enormously frustrating. I took the unprecedented step of upgrading to Windows 8.1 to ease some of the usability headaches.

Except that it took three agonizing tries before it worked. The first two times it spent hours and hours trying to upgrade but failed utterly, I mean black-screen-with-blinking-cursor utterly, and I spent hours and hours restoring my laptop to Windows 8 so that it would function. It was an ungodly, gory mess. I gave up and planned to just stay on Windows 8.

The third upgrade try happened involuntarily. One day my laptop announced that it had downloaded 8.1 in the background, and that the next time I restarted, it would install itself.

Nooooooo! I scoured the Internet trying to figure out how to prevent the upgrade, but found no help. I felt doomed. And sure enough, upon reboot, it went into a long dark night of upgrading.

This time, finally, it came back with Windows 8.1 installed. But hardly anything worked. The display was wonky, my wireless mouse was unresponsive, I couldn’t connect to my printer. I had to update a whole bunch of drivers and change a whole bunch of settings, and finally the laptop worked again.

I was relieved, but resolved: never again!

My favorite sippin' glass
Bourbon: essential to any Windows upgrade

So when Microsoft announced Windows 10, I wasn’t very excited. My laptop was working okay on 8.1, and I was perfectly happy with Windows 7 on my old desktop. But the more I read about Microsoft’s plans for Windows, the more it became clear that Microsoft was changing its ways to not support old versions of their software for years and years anymore. To keep getting good security updates, the day was coming when you’d need to be on the latest version of Windows. The writing was on the wall.

So I reluctantly decided to test the waters on that laptop. I started early on a Saturday just in case I needed to spend the day troubleshooting.

I started the installer. I stood by, my anxiety building. And then an astonishing thing happened: it went flawlessly.

The installer showed me progress every step of the way. It rebooted the computer several times, but each time it came back successfully and kept going. And then it rebooted one last time and there was Windows 10! And everything about my laptop worked properly. Elapsed time, less than 30 minutes.

And then I liked Windows 10. It was enough like Windows 7 that I didn’t have to relearn how to use my PC, but was fast and stable and had some neat new functionality that I wished my old Windows 7 desktop had.

Before long, my Windows 7 desktop notified me that it had downloaded Windows 10 and would upgrade as soon as I gave the word.

Fear stabbed at my heart. My desktop PC was reasonably well tricked out when I bought it — Intel Core i5, 8 GB RAM — but was getting up there in years. I’d installed and uninstalled all manner of software on it. My kids had installed all sorts of games on it and had surfed their way into a couple viruses I had to clean up. So this machine wasn’t exactly pristine. And this PC is the hub of my digital life. All of my photographs, all of my writing, all of my financial and personal files, everything is on it. I have good backups, but they didn’t entirely salve my anxiety. So I waited.

Over the next few months, the popups kept coming: Are you ready to upgrade? Windows 10 is all downloaded and ready. All you have to do is click here! Click the button! The beautiful, shiny button! The jolly, candylike button!

One night I sat down to write. I’d poured myself a bourbon (good stuff — Woodford Reserve Double Oaked). It was busy lowering my inhibitions when Windows popped up another invitation to upgrade.

I was tempted. I poured myself another bourbon, a double. And then, impulsively, I clicked the button.

Instantly, I was flooded with regret and anxiety. But then the install went as flawlessly as on my laptop. It took a little longer, about 45 minutes, but my PC came back up ready to go.

There was one small hitch: my mouse’s scroll wheel no longer worked right in Chrome, and only in Chrome. Updating the driver solved it.

I’m impressed. Microsoft, my hat is off to you. I don’t know how you did it, I don’t know what has changed inside your organization, but this was a great upgrade experience.

By Jim Grey

Writer. Photographer. Leader of geeks.

10 replies on “To Microsoft: Kudos on the Windows 10 upgrade experience”

Great to see Microsoft go this route as well. Apple comes out with a new major version of the OS maybe every year and the updates generally work fine. Sure a few apps have problems but then you shouldn’t update right away anyway but wait for the first point release. 😉

That said, Apple is in the business of selling hardware so the rules are a bit different.


“Bourbon: essential to any Windows upgrade.” The same is true for many of us Mac users too, Jim. But I’m relieved to hear that your latest experience has been positive. It’s always a pleasant surprise when companies actually get it right, isn’t it?


I expect Mac upgrades to go flawlessly, too — but I’ve had enough “Dinah, bring me the bourbon” moments to know otherwise. 🙂 To be fair, most of the problems with my MacBook have been software interface issues, rather than the kind of major OS meltdown you experienced (poor guy). But Apple’s iOS is another matter. THAT seems so consistently rushed to market, with the “let’s let our users do the Beta test” attitude you described in a previous post, that I now wait several weeks after a new major release before I even think of upgrading. It does frustrate me, though, that the “upgrade now” button is so darned persistent. I feel as if I have to be extra-vigilant to avoid accidentally upgrading to a new OS. It’s not very good UX to feel as if you’re constantly at risk of being tricked. Sigh.


I always wait until x.01 is out before I upgrade my iPhone, too. My very first iOS upgrade FRIED MY SIM CARD. Yes, you read that right. The part of me that’s OCD absolutely hates seeing that red 1 on the Settings icon, taunting me…….but I’ve learned to be patient.


My mind is reeling trying to figure out how an iOS update could FRY A SIM CARD. (Insert bulging-eye emoji here.) That’s the best argument my OCD self has heard yet for ignoring that pesky red “1” for a while!

Liked by 1 person

I’ve adamantly decided to wait until the very last minute to upgrade any Win 7 machines to 10 (for free) – way too many reports of botched upgrades (the OS gods were apparently giving you a break) and forced updates that break things – so they have maximum time to get their ducks in a somewhat straight line. And I have zero intention of upgrading my personal laptop. Of course, I have yet to see a Win 10 nagware popup so it’s not hard to ignore. 🙂


Hunh. I’ve not exactly scoured the Web for reports on the upgrade, but what reports I’ve come upon have all generally been positive. And Michael, if the upgrade could work as cleanly as it did on my crufty old desktop, I’d have to think it’s a mighty solid upgrade.


AskWoody (dot com) keeps me up to date with most Windows issues. He’s also written pretty much every Windows X for Dummies book.


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