Windows 11 not the worst Microsoft desktop OS experience ever at least in one key area

If you think you have compatibility issues on Windows 11 and that makes it the worst Windows ever, you may need to think again.

These days, after massive criticism from users, Microsoft says it is busy fixing Windows 11 and improving its performance. Bugs and issues pop up quite commonly at the moment, and just this week itself, Microsoft admitted that one of the recent updates it released broke one of the most useful Windows 11 Start menu functions, as the Start menu no longer worked properly after it. While this was clearly Microsoft's own fault, a veteran engineer at the company, Raymond Chen, recently blamed users for the problems and issues, suggesting that a lot of that is often down to user error.

Regardless of whose fault Windows 11 issues may be, Chen has published his latest article this week, where he took a trip down memory lane, back to the Windows 3.1 and Windows 95 days, and talked about massive compatibility conflicts that often arose between the two OS during the transition days.

Chen has revealed that some Windows 3.1 programs were so tightly bound to the old system’s internals that they simply could not make the passage to Windows 95. He explains that the problem lay in how certain developers had written their software, as instead of relying on documented APIs, they converted system handles into pointers and manipulated internal data structures directly. This shortcut worked under Windows 3.1’s 16‑bit heap, but when Windows 95 introduced a 32‑bit heap for user interface and graphics objects, those no longer functioned as intended.

Hence, at least in the case of compatibility, Windows 11 users probably do not have it all that bad as aside from Microsoft's own stringent system requirements, most people have not had to deal with such compatibility-related problems.

For those not familiar, Windows 95 made a massive leap in visuals from Windows 3.1 as it introduced a GUI (graphical user interface) and thus had to upgrade to a 32-bit design since it needed much more hardware resources.

Chen has added that Microsoft did try to ease the transition using a sort of patch. For this, a system was built to help legacy applications run on the new platform, and many quirks could be handled. But some failures were simply hopeless, and one such case involved a program that performed strict version checks such that if the OS wasn’t Windows 3.0, 3.1, or 2.1, it assumed it must be Windows 2.0. As such, that logic rendered it incompatible with Windows 95 by design. Aside from that, some other apps failed because they bypassed APIs in unsupported ways, a practice that didn't play well under the new architecture.

While the problem was not inherently Microsoft's fault, from a user's perspective, a bad experience is just that, a bad experience. So when many feel like Windows 11 is the worst out there, it does suggest that users may be viewing the past with rose-tinted nostalgic glasses, as Neowin reader leonsk29 points out.

If you found this story interesting, take a look at the other stories about Windows 95 we have covered in the past.

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Posted Thursday 9 April 2026 at 5:49 am AEST (my time).

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