this post was submitted on 10 Dec 2025
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Realistically, comfort comes from experience. The more you use it the more you'll feel comfortable.
If you want to get a lot of exposure without dedicating too much time to it and limit the risk, I would say, spin up a Debian VM and try to configure it into the server you want the old school way. Setup ssh keys, raid pool and samba share all via ssh. Try to do it like you're actually deploying it. This will give you real world exposure to the command line and the commands you'd run. Next maintain that server like it's production, ssh in every couple of weeks to run updates and reboot. Just that muscle memory of logging in and reviewing updates will help you feel more comfortable. Do it again with another service (a VPN server would be an easy choice, a Minecraft server is also a fun one but requires a lot more memory. DNS would be good if you're feeling brave, but that's really just because DNS architecture is more complex than most realize) and maintain those servers too
Once you've setup a couple of servers and spent a couple of months monitoring and updating them your comfort level should be much higher and you might feel ready to setup some actually home production servers on Debian or the like.
You mentioned running Trunas and wanting to learn Debian and other FLOSS software, the easy button answer is to run Proxmox. Its free and open source with paid enterprise support plans available and has been rapidly improving just in the handful of years I've been running it. Proxmox is really just a modified version of Debian. They have some tweaks and custom kernels over stock Debian but impressively actually have a supported install method of installing overtop of an existing Debian install and apparently some Proxmox employees actually run it as their workstation operating system
I've actually been working my way through the proxmox-on-top-of-debian guide recently, but after installing the proxmox-ve kernel and rebooting, I was left with SSH disabled (connection refused) and no local console (more precisely no monitor output past "loading initial ramdisk"). I have so little time on my hands that troubleshooting is sometimes taking the fun out of it. Probably just going to re-install using the Proxmox ISO.
I've never tried the Proxmox over Debian method, I just know it is an officially supported install method. Good on you for getting that far though!