Sure, but at the time Windows 95 was released, they already had a couple of Windows NT releases (3.1, 3.5, and 3.51). Windows NT was a different, more modern operating system than the Windows 95/98/ME line. So, they did not have to evolve Windows 95 into a modern operating system. After ME, they 'just' switched their user base to another operating system and made this possible through API/ABI compatibility (which is quite a feat by itself).

The company that sold classic Mac OS did, too.

But you have to consider what else was going on at the time: Microsoft was actively moving away from the DOS lineage. OS/2 had been in development since the mid-1980s, and, while that project came to an ugly end, they had also released the first version of Windows NT in the early '90s, and, by the late '90s, they were purposefully moving toward building their next-gen consumer OS on top of it.

Apple needed to be making similarly strong moves toward a multi-user OS with concerns like security baked in deeply. BeOS had the memory protection and the pre-emptive multitasking, which were definitely steps forward, but I don't think they would have taken Apple far enough to allow them to keep up with Microsoft. Which, in turn, would have allowed Microsoft to rest on its laurels, probably to the detriment of the Windows ecosystem.

Really? Most people I talk with these days seem to agree that the proprietary OS is a liability.

I’ve never heard anyone say Windows is a problem because it’s proprietary. I have heard that having to pay to upgrade is a pain because you (the company) have to budget for it. Even then, you would also need to budget for the downtime and time to verify that it works before deploying the update, and both those have to be done on Linux too (it’s why LTS releases are a thing).

Anyways, Windows 10 may have its problems, but Microsoft the company is doing pretty well. Their stock is up about 50% this year (200% over the past 5). And that’s not to mention the fact that they’ve open sourced .NET among many other things.

I interpreted then as saying it was a liability to Microsoft.

Outside HN and Reddit talks, most people I know don't even care about FOSS OSes existence, they just want something that they buy at the shopping mall and can use right away.

In fairness, I don't think most people care about the OS at all, FOSS or otherwise; they care that the UI is something they can use, and that their apps work. If you perfected WINE overnight, I'll bet you could sit 80% of the population down at a lightly-skinned FreeBSD box and they'd never know.

I don't even think you'd need that for most of the population: it's been quite some time since the median user cared about desktop software[1]. I switched my parents over to a Linux Mint install a decade ago when I went away to college, and it lowered my over-the-phone tech support burden to zero overnight.

I also had (non-CS but very smart) friends who switched to (ie dual-booted) Linux on their own after seeing how much better my system was than a Windows box. A decade later, one of them is getting her PhD in veterinary pathology and still dual boots, firing Windows up only when she feels like gaming.

[1] My impression is that committed PC gamers aren't a large portion of the desktop user population, but I may be wrong.

I know a decent number of people who have That One Program that they've been using for 20 years and can't/won't leave. It probably varies by population group.

It didn't kill them, though, which was my only point. I guess HN didn't think it was as funny as I did.