Windows 11 is my daily drive. I have two Windows laptops plus a high-end Windows desktop. I pay for an Office 365 subscription. If I didn't like Microsoft's products, I wouldn't spend my money on them, especially with all the free, open-source stuff available, In many ways, Microsoft makes superior software that people think is worth paying for.
That said, there's a lot not to like. So, here are some of things I hate about Microsoft products. It is neither an exhaustive list nor the final chapter in things to hate about Microsoft products.
1. Some Microsoft products won't close on exit, minimizing to the taskbar instead. Copilot doesn't even come up with a reasonable manner to set it to close. This should be an affirmative setting. Everyone else has a way to toggle this behavior. Frankly, whatever the reason is for not having such a setting, it's really up to the user to decide if they want that behavior.
2. Office Online will sometimes insist I create a Passkey for Office 365. The ability to turn off this tendency to interrupt what I'm doing to make me cancel no fewer than three prompts is irritating. Worse yet, it doesn't go away forever. Every once in a while, it pops up again. You used to be able to turn this off, but Microsoft eliminated the setting to do so. This behavior is either bad programming or evil intent.
3. Settings on Windows, Edge, and Office keep moving around. It's nearly impossible to remember where some settings are because they are not in the same place after an update. Some products such as Edge, do this all the time. Yes, products evolve but thoughtfully not randomly.
4. On that same note, Microsoft keeps hiding settings for things like minimize on close and Passkeys. Microsoft giveth and Microsoft taketh away.
5. Copilot is too stupid to notice when these settings have changed. It constantly gives bad support information. What's worse than an AI giving bad information? Giving bad information about itself and its creator's other products.
6. OneDrive can't sync a file if it's open and hence insists on marking it as an error. Microsoft should either figure out open file sync or stop marking it as an error. One of these is personal vault which is designed not to stay open. The feature is actually an error. What?
7. Widgets are so limited they are a waste of taskbar space. Just put the weather int he lower corner and be done with it. It's the only widget anyone really uses anyway.
8. If you use an alternative browser, such as Firefox or Chrome, Windows still wants to open Edge. That's just stupid. or it's evil. Take your pick. Maybe Microsoft is trying to force Edge on those who are not into it. I actually like Edge. It has a lot of useful features I like to use regularly. If I choose differently, however, then respect that. It makes Windows seem inconsistent.
9. Speaking of Edge, they need to rationalize tab management. At the moment we have Tab Groups, Collections, and Workspaces. Each does something a little different. There is some new Copilot tab management, but I'll be damned if I can figure out how that works. I'm not motivated to figure it out because I have some many options right now.
10. Speaking of Workspaces, why don't they automatically reload/update websites when you open them? There might be some underlying technical reason but really, that's bad UX. We expect that a tab will reload when we open it.
11. Microsoft seems hell bent on gathering my private information. I'm always playing whack-a-mole with privacy settings. And those settings move around (see number three) or get hidden (see number four).
12. It's entirely stupid that there wasn't a version of Windows 11 that older machines (I'm talking machines only a few years before Windows 11) could upgrade to. A lot of folks are either stuck with buying a new machine or flying without a net now that Windows 10 is no longer supported.
13. And having to reboot after every update is annoying and dangerous. I'm betting lots of people put off critical updates because they don't have the time to go through one or more reboot cycles. Figure out how to update software in place.
14. And why do we still have to alter the registry to do certain things. This is not some kind of Windows hacking. Microsoft's own support documents tell you to do this all the time. You gotta love it when they tell you to alter the registry and then flash a "Danger! Danger Will Robinson!" message at you when you do. Seriously, there should not be a reason to monkey with the registry in 2026.
I'm sure I'll think of more. Microsoft is a big company that makes complex software. They've also adopted a bit of the Apple paternalism over the past few years. Many of the things I hate about their products relate to that behavior. I predict it will only get worse with all this AI stuff. We are going to be expected to treat tech support like a session with a therapist only with less concrete results.
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