this post was submitted on 31 Jan 2024
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Anecdote #1: Don't put yourself in a position where you've got a bunch of servers that you have to upgrade from 2008 to 2019.
Anecdote #2: The warnings against doing in-place Windows Server upgrades can't stop you if you don't read them.
What are the benefits of Windows server against super snappy Linux servers managed with docker or just an instance on a cloud provider?
In our case, there are a bunch of benefits and reasons:
We do have some systems that are on Linux (Photon OS for VMware stuff, a couple of vendor-implemented Ubuntu systems). We don't really have much to do with these system, though. I'm the only one here who's familiar with *nix stuff, and while I've tried implementing stuff like our Intranet server on Ubuntu Server, I eventually moved over to Windows Server with IIS because it was just easier for my coworkers to access and use.
As for containerization, we have so many servers that do one thing and only one thing. Docker would be awesome, but it's sadly just really not a thing in our slice of the healthcare and IT sector. We do plan to start moving to a hybrid cloud model with Azure, but that probably won't be for a few years.
LOL. The second one sounds awfully familiar. Not with Windows, but I’ve had my own cases where I didn’t read before breaking. How did it work out in the end?
Going okay so far. We've had a lot going on this week, so I didn't want to touch any of our critical systems for fear of adding even more shit to the plate for my coworkers. The non-critical system upgrades went smoothly. You can't upgrade from 2008 R2 straight to 2019, so I do an intermediary upgrade to 2012 first (hooray, the Windows 8 start screen!) VMware's mouse driver seems to break during the upgrade, and my RDP doesn't like connecting to 2012 servers, so I have to navigate by keyboard to the file explorer to start the upgrade from 2012 to 2019. There's probably a better way to do this, but I can't be bothered to find it.