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A History Lesson of modern Microsoft Windows

Reddit user “winitgc” asked the question “Why do people hate Windows 10?” And it struck me as an interesting prompt. Mostly because I don’t think of Windows 10 as being so hated. But the more I thought it through, I realized they were right. And I think I realized why. So, I answered:

Let’s ignore the “pre-NT” days (Windows 9x/Me) and just consider Windows XP as the birth of home computing for the masses. XP was ‘basically’ the primary operating system from 2001 to 2007.

When Vista launched in 2007, it was seen as a buggy mess, and people genuinely revolted. Thus, XP stayed alive in the business market.

Windows 7 launched and was everything Windows Vista promised to be, but with better stability in some of the programs that were introduced in Vista but felt “rushed” because of all of the Longhorn development failures that lead up to Vista. Windows 7 was great, but at this point, Windows XP had been in the market and WAS STILL AVAILABLE BY REQUEST to most enterprise customers and this was in late 2009 – it would REMAIN available for purchase ON NEW HARDWARE through most of 2010.

In 2014, Windows XP would receive its last update. People begrudgingly migrated from Windows XP to Windows 7. Yes, in the middle there, October of 2012, Windows 8 launched – but Microsoft’s boneheaded decision to entirely remove the Start Menu, a fixture of business computing since Windows 95, made absolutely sure that not one corporate customer was going to adopt Windows 8 if they could avoid it. So Windows 7 stuck around.

Microsoft knew that the ONLY way to avoid a situation like the 13-year lifespan of Windows XP was to decisively kill of support for Windows 7 and not drag-out extending it the way they did with XP.

Even though the 2015 launch of Windows 10 was a fair-sight better than 8 and 8.1, the enterprise world was in love with 2009’s Windows 7… and it would receive its final update some 10-years-and-3-months after its initial launch. Meaning that, once again, the corporate world would begrudgingly move to “the next thing,” but they wouldn’t be happy about it.

Nearly everyone looked at Windows 10 as Windows 7 with an app store. An app store with no apps in it. An app store which wants people to use a Microsoft account. Again, in the business world, I don’t want to be responsible for the Microsoft accounts belonging to dozens, hundreds, or even thousands of my employees. Windows 10 also saw the twice-a-year release cadence of “Feature Updates” – which was even more of a headache for enterprise customers with large networks full of computers to worry about deploying these larger than usual (and, originally, longer to install) updates.

Windows 7 had just one service pack in its 10+ year life span. The corporate world just loved the simplicity and predictability. With multiple 10+ year operating systems in the market, it’s hard to look at the shorter-lived versions and convince yourself that you want those. People don’t like change. And Windows 10, just like 7, I expect, will gradually gain a more positive reputation. As “feature updates” slow, Windows 10 will also have lasted 10+ years, from its launch in July of 2015 until its current projected end of life in October of 2025.

Normal home users didn’t like the inability to disable the automatic updates, they didn’t like not fully understanding or knowing when a new update would be installed. Many non-tech-savvy people didn’t understand the difference between a cumulative update and a feature update – all they knew was that one day the computer said it needed another update and they weren’t able to log back in to their computer for another 2 hours. The long line of misunderstanding or general lack of trust in Microsoft’s “telemetry” gathering left a bad taste in people’s mouths.

Add to all of those the other things that felt “user-hostile” such as the bloatware that came pre-installed not just from OEM’s like HP and Dell, but the Candy Crush and similar unwanted software that came with a base install of Windows, and the Start Menu being used as a place to make “Recommendations” to users… a lot of these same complaints are following through to Windows 11, right down to the “you must be online / make a Microsoft account to set up a new computer” – this was rumored to come to Windows 10, but there always seemed to be a work-around. Windows 11 appears to be forcing the issue, once again.

I myself am I self-described Windows fanboy: I’ve tinkered with every-single-revision and even every beta I could get my hands on since the days of Windows 3.11. But I fully understand why more and more people are getting more and more fed up with the decisions Microsoft is making. I have to feel, at this point, like they understand, too. This is not just them not realizing that customers don’t like the direction they are being pushed, but that Microsoft is actively pushing-against-the-pushback by enacting their decisions. There’s very much a “we know what’s best for you” attitude coming out of Redmond at the moment and we’ll have to wait and see if they learn a lesson, or if they consider their market dominance safe enough to keep imposing their will on their customers.

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