this post was submitted on 24 Aug 2026
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Just today and yesterday, one of my friends asked me to upgrade their windows server for their small business.
Installing a fucking windows took me 6 hours. This whole shit would be done in 40min I if I could install and setup Debian on their server.
I made the mistake of creating a Windows VM and believing their minimum required disk space figure of 64GB. It won't upgrade. Asks to attach an external USB drive because it lacks enough space. It hasn't anything added to it, only some bloatware removed. Attempting to upgrade takes hours, fails (despite attaching the extra storage), then restarts the entire download and install process over again. I can only assume it's incapable of caching and verifying downloaded content. There's no offline installer option, like we used to have with service packs. The whole thing is slow as molasses yet it doesn't max out the 8(!) CPUs allocated to it. The host has plenty of spare capacity. It's a steaming pile of shit.
Linux guests run fine.
I had to install Windows on my sister's computer. I also thought that since every OS is fine with my 8GB USB and minimal requirements also require a 8GB USB that it would be fine. It wasn't. I had to re-flash it on a USB meant for photos and move everything temporarily to my HDD because of that.
I think I've installed a Fedora server in 5 minutes. It's now literally 3 clicks if you're doing it manually.
Yep. Totally possible.
I'm also counting the setup and restore stuff.
It could be done in 15 minutes with Windows as well, if you actually knew what you were doing. Hell, I'll give you 40 minutes if you know what you're doing and don't have proper tools already setup.
Windows is a shitshow, but your personal lack of familiarity isn't evidence of that, lol.
I work as a sysadmin (luckily I work mostly with Linux). We have lots of tools for windows server setup on our company, and for most deployments, we have templates and checklists to deploy as quickly as possible.
It still takes at least 2 hours to deploy windows server from a checkpoint, and that's skipping all the initial installation. Most of that time is spent updating, debloating, and setting the most basic stuff up.
It takes me less time to set up a Linux server from scratch, without any checkpoints, than it takes my coworkers to set up a windows server for the 9999th time, with a decade worth of tools.
I manage multiple windows servers with AD and all the shit.
I have set them up tens of times.
When you have a shit piece of software, it is unpredictable. So you encounter a new issue every time.