---
title: "The folly of Debian major version upgrades""
date: 2025-07-13T20:35:50-05:00
topics: ['git', 'matrix', 'self-host']

---

I recently realized that my web server was still on Debian Buster, **2 whole major versions behind** the latest Debian version. Normally this kind of thing wouldn't matter to me except that my matrix-synapse server was unable to federate with matrix synapse servers running newer versions. I normally run rolling release distributions on my local machines (I use Void btw) and it had been a long time since I tried this kind of upgrade. I went in hopeful that it would be straightforward. 

 **This is a reminder to backup consistently.**

Of course after thinking everything went fine, I tried to install a new package and libcrypt ends up getting removed leaving me unable to login to my server. Luckily I had backed up before this which saved all of my bespoke configurations. I'm sure no one noticed the down time but I did use this as an opportunity to make the followjng changes:

- matrix-synapse upgrade to dendrite for better performance. 
- Gitea to forgejo just to try something different. 
- Properly set up actions to auto build and deploy site on push. 
- Rework website and swap to the [terminal hugo theme](https://forge.alexselimov.com/aselimov/Terminal-Hugo-Theme)

So far, I have positive opinions of all of my changes and highly recommend dendrite and forgejo.

**Note to self: Never consider it upgrading Debian version. Always structure it as a migration to newer Debian version to avoid downtime**