Windows 95 was pretty much broken “by design”. This is truer than it seems, especially if you skip being charitable by taking the context into account, namely that Microsoft mainly designed Windows 95 for compatibility. (The contemporary Windows NT on the other hand was a much cleaner design, though still questionable above its kernel layer).
You might now ponder whether a broken login screen, i.e. temporarily not being able to access data, is maybe better than downright losing it, but my point was more that I sometimes get the feeling that earlier MS DOS/Windows OSes are now seen through some kind of nostalgia glasses, that seem to make the OSes much more stable and put together than they actually were.
In my experience, most somewhat mainstream OSes were much less shoddy. This includes various Unixes and Unix-likes, but also OS/2 (which was jointly developed by Microsoft, with IBM).
Can you share specifically what did those OS exactly break back then? And were the breakages more common than competing OSs used in similar fashion?
My memory of those OSs things would break due to the drivers and hacks of third party SW, not due to things MS was shipping like today.
I was doing random college kid stuff:
* Surfing the web
* Using Eudora lite for email
* Playing Quake1 and GLQuake, probably some Quake 2 and StarCraft around that time
* Using mIRC a ton to chat on undernet
* Using Xylinx to do my coursework for CS314
* Using MS Visual J++ do do more coursework (good riddance!)
* Writing papers in (I think) StarOffice, but it might have been just "Word" at that point.
Looking back, the writing was on the wall...
* at "random", during regular use
* when installing something, sometimes
* when removing something, sometimes
* slowly, over time
They were essentially just huge steaming piles of shit.
What you are describing was true at the time for Linux. It was an absolute bear to set up (at the time of win95/98) if you had anything unusual but once it ran it ran.
This has never been true for windows although the reasons why have shifted over time: it used to not work primarily because it was just shit. Now it additionally doesn't work because it is actively malicious.
I am writing this from the perspective of someone who is regularly forced to use Microsoft's products for work. I am familiar with the subject matter.
Windows was always buggy as hell, but windows updates didn't break windows as often and most importantly they were also optional. For decades people would go online on Patch Tuesday to look to see if people were reporting problems with the newest round of Windows updates. Maybe there'd be a problem with an update and a specific network card, or a certain video driver, but Windows didn't usually break Windows.
Even if it did, you at least had the option to just not update. These days Microsoft doesn't care about problems with their updates. Even when they are warned ahead of time that there are problems they're happy to shove them down our throats, at any time of the day or night, and break Windows or even delete your personal files (https://arstechnica.com/gadgets/2018/10/microsoft-suspends-d...) in the process.
Out of all the vague and unprovable things that never happened, that one never happened the most.
I'm sure you can find users on any OS complaining with "random" breakages but unless you can show any data that proves it was due to the OS and not your HW or third party apps or your own actions, this means nothing.
And where's the proof/documentation for this, if it's as common as you suggest?
If it were a design problem as you say, then everyone would have the exact same failures with the same incidence rate, but they don't.
The shocking negative was the amount of ads and tracking I had to get rid of, like chinese budget phone tier of crap.
Once you get rid of that though, the experience is halfway decent. But there are absolute head scratchers for 2026: some dialogs literally blurry because they haven't adapted them to my 4k display, apps adding itself to self start at boot left and right, and so on.
The most laughable event happened after I installed windows home when my license was for windows profesional. The official way to solve this was... to turn down wifi and write a hardcoded switch-to-professional key as a fake activation. That was the most amateur workaround I've seen in decades.
Windows is amateur hour when it comes to 4K support. They have rewritten some applications recently and they are hilariously broken. Like the task manager or the freaking start menu. If the scaling changes once they’re running, they end up a blurry mess.
Also, the task manager never recovers after changing from dark to light mode or vice-versa. The start menu is broken the first time it opens, but it then recovers.
The taskbar sometimes shows the icons at the wrong scale, so you have these weird mis-aligned portions of icons.
At this point I’m wondering if anyone in Redmond actually uses this OS.
It may not be the bean counting optimal, but it is a long term image they project of the company.
I'm in the latter category. As a Sunday photographer who daily drives Linux for work, I can't justify investing in Apple hardware. I used to daily drive macs, so I'm not against Apple on principle, but for my current needs it's just too expensive, since for my actual work Linux works better for me and the hardware is free (through work). Since I don't spend 8 hours a day using Windows and my income doesn't depend on it, I just put up with the shoddy quality. I can do what I need with my photos and it's good enough.
Overall, it's an absolute joy.
It just works extremely well.
Like any new platform it has its fair share of quirks and inexplicable behavior. My two biggest pet peeves are magic interactions that are very useful, but I don't know how to repeat (my recent downloads file things disappeared from by dock on the last reboot), and extremely missable interactions (apps asking for the permission to send notifications is an extremely missable notification that you have to hover over -> Options -> Allow).
However, at the end of the day, these are all things I can learn. A few I can change with Vorssaint.
The issues with Windows and desktop Linux are much much deeper than that.
Anyway, this is not a call for you to start listing all the stuff that's broken (though feel free!), I'm just amazed that, with years of power and freedom on Linux, you truly enjoy Mac more. Just goes to show each of us has our own workflow and tastes!
And more importantly, MacOS (like Windows) are still poorly translated compared to your average Linux desktop with some leftover always in English. It's okay for me as a software engineer but it's not acceptable enough to give to my parents.
* There is only one systemd --user session per user with one D-Bus instance. So you can only have one desktop instance active at a time.
* There is no way for privileged apps/scripts to generically control the desktop or other apps in Wayland. (so no accessibility, AI computer use or even general scripting)
* There is no differentiation between configuration that should be active on (user, machine) tuple, and configuration that should be active on (user, *) tuple. (even Windows gets this right!)
* Desktop apps do not report rich activity information so they cannot be smartly memory managed.
* Desktop apps cannot generally be restored after getting killed/system shutdown.
* No application identity, PIDs voluntarily take on application identities in Wayland and on D-Bus, but PIDs that don't can easily escape observability, and if they consume resources but not enough to show up high in top, good luck knowing about them.
Which is an interesting assertion by itself, since I have a local deep-seek model that routinely uses scripting to fire up servers, browsers, take screenshots, and assess how it's converging on a solution. I'm sure there's a long discussion to be had about how all of that is just a dirty hack, but for my purposes, it's been working excellently.
For me it's worse: I grew up on stuff like the C64 and then the Amiga. Switching to DOS was a serious step backwards.
> I have to ask when was Microsoft above breaking things?
Never: they've always been mediocre.
> As soon as MacOS (OS X) was a viable alternative I gleefully switched and never looked back.
I switched to Linux in the early Slackware days (then Debian 1.1). Most of the world followed and now tens of billions of devices are running Linux, not Windows.
I am happy to tell that gaming is in pretty good state in Linux these days.
It’s so bad, the windows engineers in my company are on MacBooks and work in jump boxes.
I was a wuss and waited for a CD. I doged the 98 floppy install....
That betrayal was arguably the first step towards the near-total enshittification of Windows that we see today, if you don't count the introduction of product activation with Windows XP.