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In direct contrast to macswitcha2's question about favorite macOS versions, what was your least favorite Mac OS X/macOS version(s) over the years, and why? (Classic Mac OS versions also accepted.)

Mine was Mavericks (horrid, buggy, overall a sloppy mess), High Sierra (performance issues, very buggy, had to do quite a few reinstalls), and Catalina (similar to High Sierra). I do faintly remember System 7 being pretty bad, with numerous crashes.

Edited to change System 6 to System 7; misremembered initially.
 
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I have Catalina running on my 2012 MB Pro with 16GB ram, installed without issue, runs as smooth as silk...
 
The 7.5.x series was quite horrible. It added neat features (most of which were heavily underexplored: Apple Guide, for instance), but needed multiple updates to get an acceptable level of polish.

In the modern era, I'd say Lion launched prematurely; Mountain Lion then fixed a lot of the severe issues.
 
Probably 10.0. The excitement of the public beta had worn off and the reality of a painfully slow OS with missing features (rebooting to OS9 to play a DVD!) set in
 
Yeah, 10.0 was rough. It did have Docklings, though. Impractical, sure, but cute to look at.
 
Least favorite?

Mavericks.
Never got it working smoothly, even on an experimental drive.

Looking forward, the entire m1 OS "paradigm" (protected boot partition, no more "internet recovery", etc.) looks like it's going to be more trouble that it's worth.

I'll be sticking with Intel Mac hardware and Mojave for the next several years to come (at least)...
 
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I’ve only been using Macs since Snow Leopard and have never really found any release that made my machines particularly buggy or slow. My problems have always been with iOS releases.

So my least favourite macOS would have to be Big Sur, which is the ugliest in my opinion.
 
So my least favourite macOS would have to be Big Sur, which is the ugliest in my opinion.

Different strokes, indeed. I like the look of Big Sur, as the cosmetic deltas between macOS and iOS/iPadOS were starting to drive me a bit bonkers.
 
Different strokes, indeed. I like the look of Big Sur, as the cosmetic deltas between macOS and iOS/iPadOS were starting to drive me a bit bonkers.

I think that it feels further away from the aesthetic of the apple eco system now. With it's throw back to OS X aqua design, with the 3D effects on a lot of the icons. If they had just used the flat, non protruding icon design language of iOS, it would have looked a hell of a lot better.

But I liked that macOS had it's own icon identity. Just like watchOS and tvOS still do. They are different (as they are displayed and used differently) but they obviously belong to the same family of software.
 
Mavericks left a bad taste in my mouth still
maybe
Mountain Lion was great tho!
Mojave is incredible!
 
Never had issues with any till Big Sur. 8 month old MacBook Pro and things are broken. auto dim is horrible, air play gone and mirror does not shut off all the time
 
Mac OSX 10.0 was the worst "user experience" of them all for me, including pre OSX-era OS versions. Mac OS Lion was the buggiest and least compatible version for me.
 
Didn't use 10.0 so can't speak to it. Lion was absolutely horrible for me until 10.7.3/10.7.4, after that it was usable although I still wasn't a huge fan of the OS (Save As gone, dumbed-down aesthetic, Spaces not properly replaced). Mountain Lion was much better overall. Never had the major Mavericks issues others did. Yosemite beach balled a ton for me but it wasn't buggy.

Catalina and Big Sur have been quite troublesome for me even on the newest iMacs that support it. Music is unusable. It doesn't work properly with my library at all and even when I do play something it's horribly crackly for some reason. Not willing to give up my library so my 2020 iMac has seen much less use than it otherwise would've. I don't need a computer for work anymore so all I care about is getting my music in and having a stable web experience. All else is secondary. Big Sur aesthetic is also ghastly.
 
I have Catalina running on my 2012 MB Pro with 16GB ram, installed without issue, runs as smooth as silk...
With the last update of Catalina, it runs smooth as silk also on my MacBook Pro 2018 i9. Probably depends on what system it runs on.
 
During the limited time I had Catalina on my 2020 iMac it was performance wise quite good. I hated music but it wasn't any more buggy than the obvious ones. Big Sur was completely decimated with bugs by comparison for me on the same machine. I'm selling the iMac, but if I were to continue using it I honestly would attempt a downgrade.
 
I think I still have my 7.5.3 instal disks somewhere... all 37 of them! (Ok, I think it was 11?)

Every OS has its pros and cons... I think quite probably your machine has a big impact on your experience. For example running System 7 on a Mac Classic with only 2MB of RAM was painful, but when I upgraded to an LCIII with 4MB of RAM, 7 was fine.

10.0 to 10.3 were crap...
 
My first Mac was a Classic I bought at a yard sale for $20, back before they were worth anything. Wrote my school stuff on it in Grade 8, hard drive failed, and I didn't know about the whole boot-to-firmware magic trick they had. Ended up recycled. Mac OS 6.x was alright. Slow as paste on the 2Mb of RAM I had.

My least favourite Mac OS of the modern era was Leopard. Tiger was smooth, relatively pretty, and did everything I needed it to do at the time, but Leopard was a slow, bloated, overwrought mess on the Mac I had at that time, an iBook G4 1.42.

Then I had Snow Leopard on an Intel Mac and it was night and day.
 
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