When looking through the history of Windows, some of the major milestones included the very concept of a windowed user interface in 3.1, refining the concept into a complete desktop-oriented (as in, a physical table top, with files and folders and a recycling bin) experience in Windows 95, huge backend improvements in the kernel (eg networking) by merging in the NT kernel (last used intact in Windows 2000) and giving us Windows XP.

Note well that XP was the first juncture between a consumer-oriented OS (a la Win 95/98) and a business-oriented OS (a la NT Server or Windows 2000). The missing link here is Windows ME, which was the next consumer OS after 98 but it flopped so hard when it became apparent that this artificial consumer/business division wasn’t going to scale. Specifically, the Windows 9x kernel had too many DOS-isms whereas the NT kernel had no such issues. Hence, Microsoft undertook the massive effort to bring the two kernels together for XP.

In that sense, XP coupled a newer kernel with a polished UI. In essence, the company bet all its chips on XP. And fortunately for them, it paid off. But this came with a cost: XP has to carry the lineage of both the DOS/95/98/ME and NT/2000 into the 21st Century. This means the same OS has to support things like Active Directory (a feature only used by corporate customers) and Fax for Windows (used by anyone that wanted to use their dial-up modem for faxing, but also on fax servers, which are somehow still relevant today), while also supporting DirectX for the consumer gaming segment, plus multi-user support for “home computer” customers that still share a single machine for a household, despite a market trend towards personalized computing, and everything else under the sun.

And that’s before we get to some of the backwards-compatibility support they still have to upkeep, like 32-bit support on the x86 family of CPUs, and BIOS (in spite of UEFI being a decade old). Notably, Windows on ARM has never kept such backwards compatibility, with ARM32 being completely deprecated and only ARM64 being supported by Windows 10 and beyond (hence, Windows on Raspberry Pi).

And then, of course, the Microsoft own-goals and mistakes: somewhere around 8.1, they decided to meet the tablet/touchscreen market by having Windows be touch-oriented. But as was blitheringly obvious then and now, the desktop concept cannot possibly be similar when the controls (keyboard/mouse versus touchscreen) are swapped out. Thus, this compromised the desktop experience in pursuit of a relatively niche target market.

A better execution might have been to port Windows for ARM (which is what most/all phones and tablets use today) earlier than they did, use that as the basis of a tablet-experience OS (like how Windows Media Center was just an application atop Windows XP), and then later introduce compatibility with desktop apps (like how Apple can now do full-speed x86 emulation using special ARM extensions baked into their custom silicon). That said, the latter was only technically achievable in the 2020s, but seeing as Microsoft was the market leader well into the 2010s, they would have been in the same position as Apple is in today.

So to summarize my long-winded comment, Windows carries a lot of weight. It is the result of successfully merging two very-real market segments into one product (business users and consumer users), then MSFT dropped the ball by chasing the Next Big Thing and adding more diametrically-opposed objectives to an over-burdened OS, with nary a plan for how to eventually relieve it. Had they instead did a separate OS for tablet and mobile (rip Windows Phone), they could have merged that one into the XP-based kernel and got the refined best-of-both-worlds.

Instead, they now have the worst of both. The Windows 11 desktop experience sucks, with bad icons, near-invisible text boxes, confusion where there wasn’t any, and all while pushing consumers towards web browser-based apps. And to make it sting harder, because they’ve been feeding this mess to their corporate customers, those customers now demand that everything be kept the same (“better the enemy that you know”) which prevents Microsoft from making XP-level wholesale improvements.

They’re stuck, they know it, and they can’t really fix it unless great leadership shows up to take command of the ship. But similar to Amazon (which makes most of its revenue through AWS, not selling/shipping products), Microsoft makes the majority of its revenue in two segments: Azure cloud and Office 365. It’s hard to revamp Windows when it’s now playing third-fiddle.