Unfortunate Windows Server experience, and *so* easy to get right
I do a great deal of remote administration for customer systems, which means I have to install updates and reboot periodically. Dozens of times a month.
But when I have multiple sessions going at a time - which is super common - and am rebooting machines here and there, Microsoft's messaging is remarkably unhelpful given how easy it would be to get this right.
Requesting a restart is done from the Start menu, and is easy and routine:

Easy enough, right? But when I have a bunch of these in flight, and the confirmation looks like:
Wait - what? Shutdown?
I have to stop every time to make sure I'm not shutting down a customer's system and only restarting it like I requested. I've actually shut down a customer's machine once, and was grateful that it ended up not being a big deal, but it's maddening that something so easy to get right isn't done right.
For sure, Microsoft has a substantial complication regarding localization, putting the messaging all in the proper local language, but this is high-consequence messaging.
Really, Microsoft: you can do better.