Took some time to redeploy my web server. It’s been running on Debian 13 since that came out, but now its running Debian 12. Yeah, I went backwards a version, because I don’t really like 13, and where Debian is going.
The Issues
The two main issues I have is Tailscale magic DNS, and where it looks like Debian is heading.
Lets start with the Tailscale issue. When you have a machine on a Tailscale network, you don’t have to use its IP to connect to it. You can just use its name on the tailnet. For example ssh nt@nt-prod-fastfinch. This is great and all. And it has worked flawlessly on everything I’ve put Tailscale on. Except Debian 13. There, it’s kinda hit or miss if it works, or throws a DNS error. And seeing how I reverse proxy some things through my VPS, yeah. I had to put the Tailscale IPs in for those in my Caddy config. A pain if I redeploy those. Before, I just have to give the new deployment the same name, and traffic would flow to the new host. Under 13, I had to update the IP in my Caddy config.
As for where Debian is going… I don’t like it. They seem to be going down the path not of wanting certain packages, due to very non technical reasons1. I’m primarily talking about XLibre, the recent fork of XOrg that has been gaining traction. Now, I don’t use Linux with a GUI, so I don’t personally care about display servers. What I do care about, is a disto not getting in the way of what I want to do, and what software I want to run. Now, Debian can basically do whatever it wants with the distro. Its their project. But, I don’t have to use it. Debian 12 has been rock solid for years, so that’s what I’m running now.
TL;DR: Tailscale DNS issues, and Debian starting to get political with their end product.
Rolling Back
Deploying the the new sever was quick and easy. Pretty much all of it (updates and package installs and configs) I have automated with a script that I curl down. After coping my content over, I pointed my reserved IP2 to the new server, and let Caddy get the SSL certs. As for the all important sever name, this new one is called FastFinch, the old one was TreeOwl.
–EDIT– I’ve migrated the server to Fedora 42, because why not. The new current name is GroundDove.