Nowadays it's the online account centric shite and all the privacy implications that come along with it. But even before that it was annoying to just trying to do the thing

Doing the thing on linux: command that does the thing
Doing the thing on windows: click here, click there, click some more, second tab, submenu, click advanced, type in the info, save, ok, "yes I'm sure", click ok, click apply, close 626254 windows, reboot

And most people still seem to prefer that because terminal bad.

Keep your files safe with One Drive, are you sure you dont want your personal home files on our cloud?

Please sign into your account again, to save time, you can always stay signed in on this device (Lie)

Your mailbox location has moved, you can use a temporary mailbox, or work offline.

We need more information from you to setup phone-sign in. Sorry, an error occurred, please contact your administrator

Welcome to the New Microsoft ___!

I am so tired and this is only my 4th year.

Clicking on a URL in a non-browser app? Surely you want to see that in Edge and not your default browser.

Yeah and every file type opening in edge for some reason? Annoying.
I'm so sick of this. Didn't they catch a lawsuit over this the first time and have to make it so you can uninstall it?

Eroding / taking away user agency. It's always little bits they chip away but over the time those chips amount to a huge cut off edge of things you cannot do anymore, or only through very convoluted and potentially breaking third party tweaks & tools. Every Windows installation ended up with a growing shit-list of things to do. Disable this, tweak that, download tool X, Y & Z just to further disable & tweak shit, and whoop-de-doo several hours have already passed when you're finally "done". Then, in the middle of doing shit, Windows update! "No! Go away!" 10 minutes later... "Hey, I think you forgot about me?" - "NO, I UPDATE WHEN I SHUT THE DAMN PC DOWN, NOT IN THE MIDDLE OF THINGS! GO AWAY!" ... "BUT HAVE YOU HEAR ABOUT OUR LORD AND SAVIOR, THE WINDOWS UPDATE?! OH AND BY THE WAY, WE RE-ENABLED OUR SPYING OPTIONS AGAIN AND WILL SEND ALL THE UNSENT DATA BEFORE YOU CAN DISABLE IT AGAIN!"

At some point I just realized that using Windows became more of a hassle than using Linux. And when you finally do the switch, you suddenly realize how fucking awesome it is that your OS is not constantly nagging you, not constantly spying on you, not constantly fighting you, not constantly changing its configuration to re-enable the things you purposefully disabled. I finally have an operating system again that does what I want it to do, a system that respects my privacy, as well as me as a user.

It gets to a point where it doesn't feel like you have control over your own computer.
For me, a big one was how it would constantly wake from sleep for no reason or to update. If put it to sleep and most times it would wake before I even s stood up from my desk. And there are settings you can change to stop that, but Windows will just randomly reset them.
And this is a really small one, but Windows 11 dropping features that Windows 10 has. It's very stupid that Windows 11 won't let you have a vertical task bar.
I've been a Windows user for 30+ years and always loved that OS until recently. But now I love Linux. An OS that truly lets me own my computer and do what I want.

Notifications, suggestions, and just generally having make the OS get out of my way so I could do what I needed.

Ads in a purchased OS.

Forced Edge openings that, as far as I can tell, can't be avoided.

This is not the kind of forced edge I like.

The search in the start menu searching the fucking web with bing instead of my computer
Accidentally hitting F1 and Edge immediately opens with some "help"

Try MSEdgeRedirect, friend. It won't stop it from opening a browser, but at least it won't be Edge.
- I switched to Linux Mint, it helped as well!

When they're not installed correctly, you can get air leaks that make it massively more expensive to heat or cool your home.

I have to use Windows for work and the most annoying thing is the OneDrive-Sync. It makes the explorer extremely slow. When I open it, sometimes it takes more than 5 sec till I can use it. Wtf is this, 1997? Another thing is Teams with the awful performance and constant design changes.

And the "endpoint protection" that scans god only knows what (sends it all online too) when you, tadam, opens the context menu by right clicking. It often takes 40 seconds.

My computer installing an update and restarting because I was away from my desk. I won't settle for any other OS though since Paint Tool SAI only runs on Windows.

That's on you. Mine's set to update at night so I never even notice.
- Ah yes. Come back in the morning to resume my work and everything is closed. Thanks, Microsoft.

To list a few:

Onedrive deleting my files
Very slow
ads
ai bullshit
updating is a pain
recall

On my old computer whenever I would launch my computer, the desktop icons would be randomly strewn around the desktop. I had to get a utility app that I would run manually every time my computer started in order to fix it.

Lots of stuff and while telemetry eventually made me quit, the most annoying have always been random performance issues. Still have to use Windows at work and I sometimes get progress bars in the Windows Explorer when accessing a fucking directory on the local SSD.

I guess this is moot for you, but for anyone else, https://github.com/File-New-Project/EarTrumpet

Having to use the wrong slash everywhere

Have you ever tried just using forward slashes anyway? It works more or less some of the time.
- Yes, except where it doesn’t, which you have to remember, which makes it just another annoyance.
I'd actually like it if it was backslash for local paths and forward slash for remote paths. But if you connect to a cifs share, it still uses backslashes, so the whole thing seems pointless

I can't launch minecraft without first opening the microsoft app store signing out, then signing back in.

MS Edge, its a good browser. But fuckin hell does Windows love to shove it in your face every chance it gets.

Use MSEdgeRedirect to use your default browser.

it feels like the natural result of corporate agile. dozens of teams doing little pieces with one dude making each smaller part all on their own. then someone just overrides the merge rules. and now i'm stuck trying to follow the ravings of angry lunatics all talking at once. i just want the os to shut up and do what i tell it to do. and i absolutely do not want it to start pretending its alive with some stupid chat bot ai nonsense.

A lot of software did not run under windows NT4. Especially stuff that used the soundblaster directly.

Plug-n-play never worked, and drivers for hardware usually only came on floppy for DOS/win3/win95.

For some reason USB-drivers were not installed by default, either. That's after swapping through 18 diskettes during installation. Just copy it all if you're going to have me be a human jukebox.

OneDrive, I fucking hate that thing. Rest I can tolerate but OneDrive really grinds my gears.

'contact your IT admin'

Great suggestion when you are the IT admin, lol

The fact that it isn't open source and costs money to use. I actually like Windows over Linux even as someone who has written Linux kernel drivers for a living, or maybe because of that but the fact that I can't poke around the code and improve the system is annoying to me.

It's also why I'm working on a project to develop my own OS from scratch that has a better design and programming interface than POSIX and Linux respectively and is easy to use like Windows. It's not an easy task but certainly a worthwhile one IMO.

The lack of primary selection/middle click paste. I select text, try to paste it and then have to sheepishly go back and actually copy it for realsies.

I used to get annoyed at the lack of multiple workspaces, but since switching to a multi-monitor setup, I don't really use multiple workspaces any more.

Windows 10 had multiple workspaces. Presumably they've kept that.

Ctrl+c not copying on rare occasions. Even if it's my keyboard's fault, it could be avoided with some visual feedback to confirm to me that ctrl+c was registered ans clipboard was updated, so that I'd immediately know that it didn't work after pressing ctrl+c, rather than later when i switched to a different window/tab and pasted the wrong thing

The fact that i can't route audio between apps (without 3rd party closed-source apps). Why is something so basic not included into the system?

Registry

As a c++ dev: winapi. Right away you are greeted by windows.h adding loads of macros with common identifiers without any prefix to your preprocessor. That's a sign of things to come for anyone who has to use it. Maybe that explains lack of open-source audio routing apps: nobody wants to deal with windows driver development for hobby - and if that's the case i sure can't blame nobody for that.

Copy not working is becoming a frequent issue
windows.h without NOMINMAX be like
"hippity hoppity words min and max are my property"

Being told I should switch to linux

Sometimes friends, in their curiosity, come up to me and ask me, Jordan Belfort-style, "Sell me ~~this pen~~ Linux." Why do I like it so much, they wonder?
And I always tell them:
"Linux is like... the vegan OS. (bear with me) Mac and Windows people don't really care about OSes. People who switch to Linux either find they couldn't be assed to deal with it, or they love it, and those who love it love it. Then they always tell people lol.
A good thing though: because everyone's such an opinionated nerd, the lateral set of problems you run into won't be 'solved' by random Microsoft Forums /sfc scannows or arcane regedits, but by a nut who debugged the entire thing 30 minutes after the bug came to exist to find a workaround. True story.
Buuuut Linux is more of a lateral movement in terms of problems, it's just a tool after all. You solve Microsoft Recall and start menu ads but run into new but tiny annoyances. I find Linux problems easier to fix than Windows ones because of the nerd army thing but if your Windows setup works for you, it works and that's really all that's important. If you do start Linuxing though you'll learn a lot just by osmosis."
And they usually laugh and decide to keep their routines in place. Don't hate me vegans.

I have to use it for work, and I hate how links to other apps, say a Teams meeting, dot open up the app. Rather, they open a new tab in a browser, only to open the app while leaving a blank open tab in the background. It’s just sloppy as hell.

My default browser at work is Chrome. Microsoft Teams and Outlook open links in edge anyhow. I wonder why!

I hated having to do everything in a window. The desktop wasn't really a thing.

https://youtu.be/oz3YuWfaKvI

A nonsensical amount of filepaths absolutely fucking everywhere to check for things.

Having to verify something installed/uninstalled correctly.

Pushing the button that says it does a thing, and it not actually doing that thing.

It's rare and fixable, but every now and then I download a file and it just fucks up my icon cache and makes Explorer practically impossible to use. Some other issues I've encountered is that if you have a ton (and I mean it, over 10k) of fonts, then apps in general start lagging (VLC and Figma are the ones most affected by this), and that Defender is a bit too good and causes certain apps to lag like mad since it sandboxes it iirc

I've spent the entire morning trying to install sql 2022 and it fails on a mysterious error message. The suggested fixes don't work.

I'll have the same problems on Linux occasionally but at least I did not pay to have those issues.

Why in god's name does it rearrange the order of programs on the taskbar?

Annoying little quirks of text highlighting and navigation. Oopsie, you moved an extra quarter of a centimeter to the left of the paragraph you tried to highlight starting from the bottom. That means you want everything, right? Yeah we're highlighting everything. And so on.

Fortunately I've picked up some workarounds over the years:

Trying to highlight text in a hyperlink: hold alt

Methods of selecting text blocks (e.g., when normal mouse-select is doing bizarre stuff):

Try highlighting from end to beginning
Click point A, hold shift, click point B
Double-click first word of desired selection to highlight it, or triple-click a paragraph, then highlight letters with shift-right, words with ctrl-shift-right, lines with shift-down, paragraphs with ctrl-shift-down. You'll see that, for example, when you use shift-down, some text on the line following the selected line is also selected, corresponding to the length of the initial selection before the hotkey was pressed. You can use relevant combos in the opposite direction to de-select this. Or press shift-end to highlight only to the end of the line where your current selection ends, and shift-home to deselect to the beginning of the line. Ctrl-shift-end/home will do the same but for the entire page/document.
Some other useful hotkeys are available during text input -- I make heavy use of shift+pgup/pgdn to extend selections, but this seems to work in Excel, Notepad++, etc., not in this web browser text input field, for example. Holding shift while clicking also extends selections as in the read-only context; holding ctrl while clicking arbitrarily adds to selection just as in the file browser.

I don't think that's workarounds, you're supposed to use your free hand for keyboard commands to effectively highlight and edit text.
My favourite combo is ctrl+z because it reverts the last action. Works in almost every application.
Ctrl+a marks the whole text.
- Yes, these are documented features and not some kind of obscure off-label workaround. What I mean is that the use of these features serves as a workaround (or, if you like, an "alternative") when simple mouse selection should work but behaves erratically.
I don't think that's workarounds, you're supposed to use your free hand and keyboard commands to effectively highlight text.
My favourite combo is ctrl+Z because it reverts the last action. Works in almost every application.

When I was still using Windows my system would often hard crash (haven't verified it but I blame my 5700XT's graphics drivers). This wasn't an issue once I switched to Linux.

Deleting old installs.

And upon taking possession of and then deleting them how aggressively the browsers I am using are collecting and maintaining files on me. It shouldn't take 40 minutes to delete browser files from an install that only lasted 2 months.

The 3 days of settings adjustments, debloating, de-spyware-ing, regestry edits, group edits, service edits, power edits just have a functioning OS that doesn't bottleneck/ruin your espensive hardware you paid for.

Web browsers are beginning to feel that way these days.
- Meh Firefox is very customizable but not a ton of settings really for critical privacy, compatibility or optimization.
  Chrome and all Google services can get fucked for just the amount of sites, pages, sub-accounts you have to navigate thru JUST to turn off their tracking bullshit.
  I think I have my android and PC as fully isolated from any Google account, software, service or operation short of going full Root of phone and Linux. Which, Linux is on my todo list to go daily driver-Linux and 2ndary boot drive-Windows.
  For now tho, local user Windows account and all google accounts and apps either un-installed or disabled on the phone.

When it comes to installing stuff, I'm very trigger-happy. So, from experience...

Installing stuff on Windows (safely)

Hope it's on Chocolatey (choco install)
If not, search for the website online
Scroll past the AI slop and suspicious Softonic downloads
Click the website
Find the correct download button
Download
Scan with MalwareBytes (don't want an STI)
Run setup.exe
Verify PATH and wanted feature set
I do not want to bundle Candy Crush or McAfee
skim the Privacy Policy to see if they'll grind my bones to dust
Install Microsoft C++ Redistributable 2014-2018 (wtf? I already have 4 of these)
Wait
Sort the installation shortcuts into my folders

Installing stuff on Linux (safely)

paru some_software
If on AUR, skim PKGBUILD
If not packaged at all (rare), git clone it and either skim the install.sh or Makefile
Done

Did you last try windows 20 years ago or something? Windows definitely has touchpad gestures and robust window management. Dont get me wrong though, I don't like windows anymore either. Switched off it a year ago

When things go wrong in Windows at an app or third party software, stuff is often fixable. At worst you might need to reinstall the damn thing. But if the OS itself starts doing weird stuff, things often go to the headache territory really fast. Get a weird error, log says some OS component is going boom, no idea how to fix it, official instructions are along the lines of "Well if DISM and SFC are not going to fix it, looks like you need to reinstall the entire damn OS." Which usually wouldn't be a cause for anxiety, but blergh, muh preschus licence key, hope I won't screw that up.

Meanwhile, I ran one Debian install for over 20 years once. Stuff is usually very fixable indeed. There are good logs. It's rarely a complete mystery why some program is doing what it doing. At absolute worst you might need to look at the source code, which is actually rare.

Being unable to use local accounts without a ton of headache, and menus always trying to force you to use their services

Trying to install Node-GYP. Dear God the errors

Put my PC to sleep, then i go to sleep. 3am rolls around and my PC turns on and sits at the log-in screen.

This seems to be an issue only after windows 7 for me. It can't be updating because there's nothing happening when i check on the windows update, and it will do this all night until i unplug the damn thing. Then i get a couple months of this issue not appearing.

Bill Gates, except when Ballmer was there.

I can't complain. works fine for me.

ITT people who didn't/couldn't install Windows via Rufus, and/or don't know how to set up an OS