Microsoft Bob was 16-bit. Just throwing that out there.

Worst embedded OS: No clue.
Worst 64-bit Windows release: Windows 7.
Worst 32-bit Windows release: Windows 98.
Worst 16-bit Windows release: Windows 3.0.
Worst mobile OS: Android? iOS? Pick your poison.
Worst GUI: Android.

Worst GUI. OS/2 presentation manager.
Worst OS. Windows ME.
Worst 64bit. Windows 8.x.

bakemono wrote on 2025-02-27, 15:32:

Microsoft Bob was 16-bit. Just throwing that out there.

Agreed.
Unusable for anyone with IQ>80 🤣

Cyberdyne wrote on 2025-02-27, 21:11:

Worst OS. Windows ME.

Yes!
All the downsides of Windows 9x, and without the only advantage of 9x - possibility to use as DOS.

And note that it's possible to install Bob on top of ME - I once did it, as part of my Troll Build(TM) 🤣

Cyberdyne wrote on 2025-02-27, 21:11:

Worst GUI. OS/2 presentation manager.

But I don't agree with this - the PM itself wasn't bad.
It was the Workplace Shell that was mistake.

In 1992+, vast majority of brand new PCs were 32-bit - and asking for a 32-bit OS.
However, OS/2 2.x wasn't a viable option - it was sluggish, or unable to run at all because of not enough RAM.
And the WPS was a major culprit here.

For most hated windows... A tossup between ME and Vista. Vista only because "Oh, you want a driver? HAHAHAHAHAAH, no, the OEMs MUST repeat the HWQL testing process and pay us more mon-- what, they dont want to do that? HAHAHAHAH Sucks to be you!" was microsoft's STOCK answer. 8 / 8.1 gets honorable mention as being the period where "Lets make a FISCHER PRICE UI, that's fragmented and broken, because MoDeRn!" started to happen, and microsoft has consistently failed to understand that PEOPLE DONT ACTUALLY WANT THAT for a very long time afterward. Only rendered palatable by things like OpenShell.

Most hated UI?
Ubuntu Unity It can die in a fire. Win 8/8.1's fischer price UI can likewise die in a fire. Leave the damn desktop alone, you are not 'innovating' anything.

Worst mobile OS?
Windows Mobile. Designed to be idiotic from the start, with no options to control or own the device at all, and without any kind of polish to it in any capacity, making it undesirable by everyone, except MBAs who thought that being an 800lb gorilla meant that they could dictate to the market. It did not work.(tm)

"Unusable for anyone with IQ>80 🤣"
That is also valid for Android.
I would so wish a 16bit smartphone with Windows 3.x Mobile,so no Windows CE,but just real Windows 3.x with added drivers & apps & the HW for my dream-phone would be BlackBerry Key 3,so I wish the successor to Key 2 with Win16 in place of that terrible Android,the whole can be called BlackBerry Key 3.11 & a premium version would be BlackBerry Key 3.11s with solar panel built into its back side...
Just imagine,it could run on something like 386 Mobile or so...

Windows 8 and those whole charms bar thing.
It was even worse on Windows 12 over RDP connections.

win9x

Biggest time-sink with the least pay-off: Installing any version of OS/2 on any hardware

Ugliest Windowed GUI: OS/2 Presentation Manager Version 2.x (after a fresh install)

Sabina_16bit. wrote on 2025-02-27, 14:48:

Worst 16bit OS/Worst 16bit Windows/Worst DOS:
None.

MS-DOS 6.0 comes to mind - in certain configurations, "chkdsk /f" could lead to data loss, and there were also some other problems.
That's why it hastily got replaced with 6.20.

DOS 4.x was also commonly warned against - https://forum.vcfed.org/index.php?threads/wha … dos-4-xx.54820/

Not really hated, but you have to be a masochist if you try to install AIX 1.3 or Netware 286.
For Windows, I never really used Me, Vista or Win 8.

Windows 10/11. At the moment I don't even know what I will do once I can't use Windows 7 anymore.

chinny22 wrote on 2025-02-28, 00:29:

Windows 8 and those whole charms bar thing.

yes, that was a design choice for an imagined future when windows phones were around. win 10 may have its downsides but in use its a bit more like win 7 again, just slower and less tidy with more interruptions.

i'd add the initial release of win 95 which was cool looking at the time and seemed good but could be flaky and unreliable and become frustrating. win 95 became much better by win95b / osr2, then it eventually became better still (win98se)

i actually dont really like Mac OS all that much - it may be just that i dont use it much so it could just be that

Worst for user-friendliness is Linux. Without a doubt.

For Windows, the only ones I really hate are 8 and 11. Both made stupid decisions in their UI design. The other Windows OSes are good as long as you use good drivers, use appropriate software/hardware and don't install too much crap.

Honestly, of the operating systems I've used over the years, none I've truly hated.

The two lowest ranking for me are Windows ME and 8. I can't speak to 11, I'm still on 10 and will be for a long time yet probably.

My favorites were DOS and Win 9x, with XP coming in close behind. Win 3.1 was nice, earlier versions, not so much. I just stuck to DOS.

Never played with OS/2.

I'm not a big fan of "modern" Apple environments, on both PC and mobile, but it's more about how Apples does things than the OS itself. I just prefer Android for mobile and I actually liked the classic Mac OS.

Have yet to find a Linux distro I dislike, but prefer Ubuntu.

Embedded OS.... only ever used one, Win CE, and it's wasn't all that bad.

Though, back in the 90's I worked with Ladder Logic a lot, but that's not an OS. It's a GPL used in PLC's. It wasn't hard, just annoying as heck. 😜

RetroPCCupboard wrote on 2025-02-28, 09:00:

Worst for user-friendliness is Linux. Without a doubt.

"Contrary to popular belief, Unix is user friendly. It just happens to be very selective about who it decides to make friends with." 😜

StriderTR wrote on 2025-02-28, 09:34:

I actually liked the classic Mac OS

Well, I never had to use that - but if I did, safe bet I would hate it forever!

Really, an OS without CLI?
THE UTTER ABOMINATION! 😜

Grzyb wrote on 2025-02-28, 10:04:

Well, I never had to use that - but if I did, safe bet I would hate it forever! […]
Show full quote

StriderTR wrote on 2025-02-28, 09:34:

I actually liked the classic Mac OS

Well, I never had to use that - but if I did, safe bet I would hate it forever!

Really, an OS without CLI?
THE UTTER ABOMINATION! 😜

Hi, I *think* there was a CLI in the SDK for developers..

Anyway, you may have been liked A/UX. It's an Unix with a Macintosh compatibility layer and a Mac OS UI.
It could run Unix/X11 applications but also some System 6/7 applications.

https://www.youtube.com/watch?v=gFMvzysIXzY

Also most interestingly it did support Apple specific technologies such as AppleTalk and was a better network OS than real Mac OS (System).

Downside was that it did run on 68040 or 68030 systems only, because it required both a fully functional MMU and FPU. There's a small list of supported Macs.

Jo22 wrote on 2025-02-28, 11:12:

Hi, I *think* there was a CLI in the SDK for developers..

Yes, and there was third-party software providing CLI.

But there was no CLI in the system itself - and that's why that system gets bad rating from me.