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I grew up with DOS, Win 95, 98, 2000, XP and so on. I have to ask when was Microsoft above breaking things? In my mind they always had a reputation as being pre

by srmatto 17d ago

I grew up with DOS, Win 95, 98, 2000, XP and so on. I have to ask when was Microsoft above breaking things? In my mind they always had a reputation as being pretty shoddy. As soon as MacOS (OS X) was a viable alternative I gleefully switched and never looked back. I still keep a Windows machine around for gaming but I don't use it for anything more than that. All my serious work happens inside of MacOS.

worik 17d ago
I switched to Linux in 1993. Never looked back
- wolfi1 17d ago
  ah, those were the days, when compiling the kernel took about 12 hours, or the switch from COFF to elf - fun times indeed
  - worik 16d ago
    Indeed. I was a wuss and waited for a CD. I doged the 98 floppy install....
    - wolfi1 14d ago
      my first installation was a floppy installation (slackware), yeah that was an added bonus ;)
torben-friis 17d ago
I just started using windows after being on macOS since Vista. I planned to go full Linux for a gaming pc, but there are still some kinks, so dual booting it is. 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.
- vladvasiliu 17d ago
  > some dialogs literally blurry because they haven't adapted them to my 4k display 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.
  - Neikius 17d ago
    The OS is no longer a product they care about. Brings no money compared to Azure.
    - keyringlight 16d ago
      That lack of care is the part that's annoying to me, combined with them being one of the largest corporations that has the resources to throw at those issues if they chose to do so. Quality issues aside, there's lots of similar aspects like the long drawn out migration of the control panel (i.e. their own control panel applets, putting aside third party) since win8 in 2012, if they wanted they could have completed that in the last 14 years and however many major releases you count since then. It may not be the bean counting optimal, but it is a long term image they project of the company.
      - vladvasiliu 16d ago
        I think the general issue they have is that pretty much nobody who cares chooses Windows actively. It's mostly gamers, which seem to be on the way out, corporations who don't care about this, and creatives who, for whatever reason, don't want to buy a mac. 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.
bigstrat2003 17d ago
Pretty much up until Windows 10. Not that every decision they made was great (it wasn't), but they very rarely shipped stuff which was straight up broken. They used to have a commitment to quality which they threw away around the time of Win10 when they fired the QA staff.
HappySweeney 17d ago
DOS 5 was awesome. I can't recall a single bug?
- acuozzo 17d ago
  But DOS 6 was buggy as hell due to DoubleSpace.
  - vunderba 17d ago
    As a kid I vaguely remember our family had a stack of Dr. Dobb’s Journals with one particular article actually warning about the dangers of doublespace, and since it was completely optional (despite being touted as a flagship feature) we kind of dodged a bullet and had a pretty reasonable experience with DOS 6.
serbuvlad 17d ago
I've recently switched to a Mac after years on Linux, basically due to my frustration with the way the Linux desktop is being developed and the lack of quality all around for that platform. 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.
- rpdillon 17d ago
  Meta-topic: I've seen this comment many times over the years, and it never results in a discussion where folks can agree. My reaction reading it is "You must be holding it wrong!" because I daily-drive Linux in many more ways than one (servers, laptops, desktops, handhelds (Hackberry Pi), SBCs, and, Valve-willing, VR headsets), and adore the Linux desktop. I use Pop!_OS almost everywhere, but Debian/Ubuntu/Arch with IceWM or Fluxbox (or the like) works great. 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!
  - serbuvlad 17d ago
    It's a bit deeper than just a series of bugs. For all of Linux's power and freedom, its modern desktop architecture is extremely restrictive. * 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.
Lammy 17d ago
The difference is that now the breakage comes to you instead of being something optional that you can seek out or ignore. I remember installing, like, fewer than ten updates ever for Windows 95: The ‘95A’ patch, a few updates to Dial-Up Networking, WinSock update, CHM Help Update, MSXML, MSVCRT. I steadfastly avoided the webby Active Desktop IE4 ‘Desktop Update’ but did install the browser itself.
- drooopy 17d ago
  Oh, man. The "Active" Desktop. The only thing that it kept active was my CD drive when I was forced to reinstall Windows every time I tried to make it work on my PC and it broke everything.
  - Lammy 17d ago
    I was all about some 98lite ‘Sleek’ on my hand-me-down 486DX/2-66 in the late '90s, Windows 98/98SE/Me with the original Windows 95 pre-OSR2.5 non-Active Explorer swapped in :) - https://www.litepc.com/swap.html https://www.litepc.com/swap.html - http://toastytech.com/guis/l98.html http://toastytech.com/guis/l98.html
- anyfoo 17d ago
  I think people just forgot how insanely unstable and prone to breaking MS OSes were back then. Crashes and hangs that take down your entire machine were common, and “reinstalling the OS” was seen as a normal thing that you just had to do every once in a while. 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).
  - rendaw 17d ago
    But surely random crashes is better than a broken login screen that prevents you from doing any work at all?
PorciiVorbesc 17d ago
>I grew up with DOS, Win 95, 98, 2000, XP and so on. I have to ask when was Microsoft above breaking things? 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.
- krageon 17d ago
  They broke: * 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.
  - deleted 17d ago
    [deleted]
  - autoexec 17d ago
    Random existing Windows bugs breaking things, third party software breaking things on install/uninstall, and bloat causing problems are very different from Microsoft forcing an update that introduces new flaws in windows and breaks Windows in ways that had been previously working. 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-distribution-of-latest-windows-10-update-over-data-loss-bug/ https://arstechnica.com/gadgets/2018/10/microsoft-suspends-d...) in the process.
karp773 17d ago
I don't remember them being so bad. Windows 7, 8 were great. Visual Studio 6 was good. Excel was top quality for a long time. What used to be annoying to me was that Microsoft ignored the common Unix conventions for no good reason and tended to reinvent stuff. It was like smart nerds were tasked to come up with stuff without any awareness of prior art, or as if Bill G snd Steve B were trying to lock in customers into incompatible stuff. Obviously not great but working. What we get now is pure slop and negligence.
- maccard 17d ago
  The internet revolted against 8 and stuck on 7 until it was EOL’ed and went straight to 10. I don’t recall 10 being positively received, but the hate has moved to windows 11. I’m happy to be corrected though.
  - bigstrat2003 17d ago
    The problem with 8 was that the UI was designed for a touch screen without a thought given to the fact that most users were going to be driving it with a mouse. Reliability-wise, it was perfectly fine.
  - CamperBob2 17d ago
    The problem with 10 was that it was pushed as a "security update" on Windows Update. It was force-fed to unwitting/unwilling Windows 7 users like caged geese at a foie-gras farm. 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.
- Neikius 17d ago
  I remember a Windows update pushed through SBS that bricked all machines in company overnight. Boot up to bsod. Was that Windows 7?
  - karp773 17d ago
    I just looked it up. Yes, it was Windows 7. You have a better memory than me.
nicce 17d ago
> I still keep a Windows machine around for gaming but I don't use it for anything more than that. All my serious work happens inside of MacOS. I am happy to tell that gaming is in pretty good state in Linux these days.
- 0x696C6961 17d ago
  Not until the anti-cheat situation is figured out. But I play most single player games on Linux these days.
- globalnode 17d ago
  Games I cant play on Linux are kernel level anti-cheat shooters. Anti cheat should be handled on the server anyway, no one should be installing that on their machines. Everything else works great!
TacticalCoder 17d ago
> I grew up with DOS, Win 95, 98, 2000, XP and so on. 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.
Spooky23 17d ago
They really got their shit together from like 2005-2017 or so. Then all garbage. It’s so bad, the windows engineers in my company are on MacBooks and work in jump boxes.
stodor89 17d ago
"This program performed an illegal operation and will be shut down."
gosub100 16d ago
WinNT 4.0 SP6 was stable as a rock

by srmatto 17d ago

worik 17d ago

I switched to Linux in 1993. Never looked back

wolfi1 17d ago
ah, those were the days, when compiling the kernel took about 12 hours, or the switch from COFF to elf - fun times indeed
- worik 16d ago
  Indeed. I was a wuss and waited for a CD. I doged the 98 floppy install....
  - wolfi1 14d ago
    my first installation was a floppy installation (slackware), yeah that was an added bonus ;)

torben-friis 17d ago

I just started using windows after being on macOS since Vista. I planned to go full Linux for a gaming pc, but there are still some kinks, so dual booting it is. 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.

vladvasiliu 17d ago
> some dialogs literally blurry because they haven't adapted them to my 4k display 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.
- Neikius 17d ago
  The OS is no longer a product they care about. Brings no money compared to Azure.
  - keyringlight 16d ago
    That lack of care is the part that's annoying to me, combined with them being one of the largest corporations that has the resources to throw at those issues if they chose to do so. Quality issues aside, there's lots of similar aspects like the long drawn out migration of the control panel (i.e. their own control panel applets, putting aside third party) since win8 in 2012, if they wanted they could have completed that in the last 14 years and however many major releases you count since then. It may not be the bean counting optimal, but it is a long term image they project of the company.
    - vladvasiliu 16d ago
      I think the general issue they have is that pretty much nobody who cares chooses Windows actively. It's mostly gamers, which seem to be on the way out, corporations who don't care about this, and creatives who, for whatever reason, don't want to buy a mac. 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.

bigstrat2003 17d ago

Pretty much up until Windows 10. Not that every decision they made was great (it wasn't), but they very rarely shipped stuff which was straight up broken. They used to have a commitment to quality which they threw away around the time of Win10 when they fired the QA staff.

HappySweeney 17d ago

DOS 5 was awesome. I can't recall a single bug?

acuozzo 17d ago
But DOS 6 was buggy as hell due to DoubleSpace.
- vunderba 17d ago
  As a kid I vaguely remember our family had a stack of Dr. Dobb’s Journals with one particular article actually warning about the dangers of doublespace, and since it was completely optional (despite being touted as a flagship feature) we kind of dodged a bullet and had a pretty reasonable experience with DOS 6.

serbuvlad 17d ago

I've recently switched to a Mac after years on Linux, basically due to my frustration with the way the Linux desktop is being developed and the lack of quality all around for that platform. 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.

rpdillon 17d ago
Meta-topic: I've seen this comment many times over the years, and it never results in a discussion where folks can agree. My reaction reading it is "You must be holding it wrong!" because I daily-drive Linux in many more ways than one (servers, laptops, desktops, handhelds (Hackberry Pi), SBCs, and, Valve-willing, VR headsets), and adore the Linux desktop. I use Pop!_OS almost everywhere, but Debian/Ubuntu/Arch with IceWM or Fluxbox (or the like) works great. 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!
- serbuvlad 17d ago
  It's a bit deeper than just a series of bugs. For all of Linux's power and freedom, its modern desktop architecture is extremely restrictive. * 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.

Lammy 17d ago

The difference is that now the breakage comes to you instead of being something optional that you can seek out or ignore. I remember installing, like, fewer than ten updates ever for Windows 95: The ‘95A’ patch, a few updates to Dial-Up Networking, WinSock update, CHM Help Update, MSXML, MSVCRT. I steadfastly avoided the webby Active Desktop IE4 ‘Desktop Update’ but did install the browser itself.

drooopy 17d ago
Oh, man. The "Active" Desktop. The only thing that it kept active was my CD drive when I was forced to reinstall Windows every time I tried to make it work on my PC and it broke everything.
- Lammy 17d ago
  I was all about some 98lite ‘Sleek’ on my hand-me-down 486DX/2-66 in the late '90s, Windows 98/98SE/Me with the original Windows 95 pre-OSR2.5 non-Active Explorer swapped in :) - https://www.litepc.com/swap.html https://www.litepc.com/swap.html - http://toastytech.com/guis/l98.html http://toastytech.com/guis/l98.html
anyfoo 17d ago
I think people just forgot how insanely unstable and prone to breaking MS OSes were back then. Crashes and hangs that take down your entire machine were common, and “reinstalling the OS” was seen as a normal thing that you just had to do every once in a while. 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).
- rendaw 17d ago
  But surely random crashes is better than a broken login screen that prevents you from doing any work at all?

PorciiVorbesc 17d ago

>I grew up with DOS, Win 95, 98, 2000, XP and so on. I have to ask when was Microsoft above breaking things? 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.

krageon 17d ago
They broke: * 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.
- deleted 17d ago
  [deleted]
- autoexec 17d ago
  Random existing Windows bugs breaking things, third party software breaking things on install/uninstall, and bloat causing problems are very different from Microsoft forcing an update that introduces new flaws in windows and breaks Windows in ways that had been previously working. 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-distribution-of-latest-windows-10-update-over-data-loss-bug/ https://arstechnica.com/gadgets/2018/10/microsoft-suspends-d...) in the process.

karp773 17d ago

I don't remember them being so bad. Windows 7, 8 were great. Visual Studio 6 was good. Excel was top quality for a long time. What used to be annoying to me was that Microsoft ignored the common Unix conventions for no good reason and tended to reinvent stuff. It was like smart nerds were tasked to come up with stuff without any awareness of prior art, or as if Bill G snd Steve B were trying to lock in customers into incompatible stuff. Obviously not great but working. What we get now is pure slop and negligence.

maccard 17d ago
The internet revolted against 8 and stuck on 7 until it was EOL’ed and went straight to 10. I don’t recall 10 being positively received, but the hate has moved to windows 11. I’m happy to be corrected though.
- bigstrat2003 17d ago
  The problem with 8 was that the UI was designed for a touch screen without a thought given to the fact that most users were going to be driving it with a mouse. Reliability-wise, it was perfectly fine.
- CamperBob2 17d ago
  The problem with 10 was that it was pushed as a "security update" on Windows Update. It was force-fed to unwitting/unwilling Windows 7 users like caged geese at a foie-gras farm. 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.
Neikius 17d ago
I remember a Windows update pushed through SBS that bricked all machines in company overnight. Boot up to bsod. Was that Windows 7?
- karp773 17d ago
  I just looked it up. Yes, it was Windows 7. You have a better memory than me.

nicce 17d ago

> I still keep a Windows machine around for gaming but I don't use it for anything more than that. All my serious work happens inside of MacOS. I am happy to tell that gaming is in pretty good state in Linux these days.

0x696C6961 17d ago
Not until the anti-cheat situation is figured out. But I play most single player games on Linux these days.
globalnode 17d ago
Games I cant play on Linux are kernel level anti-cheat shooters. Anti cheat should be handled on the server anyway, no one should be installing that on their machines. Everything else works great!

TacticalCoder 17d ago

> I grew up with DOS, Win 95, 98, 2000, XP and so on. 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.

Spooky23 17d ago

They really got their shit together from like 2005-2017 or so. Then all garbage. It’s so bad, the windows engineers in my company are on MacBooks and work in jump boxes.

stodor89 17d ago

"This program performed an illegal operation and will be shut down."

gosub100 16d ago

WinNT 4.0 SP6 was stable as a rock