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

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

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.

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

Ads in a purchased OS.

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

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.

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

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

'contact your IT admin'

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

Having to use the wrong slash everywhere

To list a few:

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

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.

Being told I should switch to linux

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.

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.

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.

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

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.

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.

Not the most annoying, but the most stupid and simple: The fact that even in windows 10 (not sure about 11), you couldn't set custom keyboard shortcuts for volume up and down. I have had the right Ctrl+shift+up/down arrows bound to the volume up/down, since i started using Linux as my desktop fulltime over 10 years ago, and windows still won't let you do that out of the box.

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.

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

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.

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.

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.

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

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

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.

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.

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.

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

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 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.