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+layout: post
+title: Updating my servers to Trixie
+date: 2026-02-21 16:06 +0100
+---
+
+It's about time.
+Debian Trixie has been released in August 2025. I finally got around
+to gather my motivation to execute the update.
+
+I have like 5 VPS, all running Debian. Still running Bookworm until recently.
+So over the past two weeks, I upgraded the servers step by step, going with
+the "least problematic" servers first. (Gut feeling).
+
+Turns out, my intuition was relatively right.
+What confused me extremely is that the upgrade notes appear to have moved to
+https://www.debian.org/releases/trixie/release-notes/upgrading.html.
+Previously, iirc, it was always a chapter in the Debian Handbook.
+
+So, the pain points of Debian updates, for me, always is the config file
+updates. Usually, I want to keep my changes, but use some of the
+package maintainers changes. It's frustrating for me that Debian asks me for
+a decision in the middle of an upgrade. I'd actually like an option,
+"just continue with the upgrade, keeping my config, for now". Which
+could be problematic for major upgrades with option deprecations I guess?
+There probably is even some option for this (dpkg-reconfigure debconf?),
+and I just haven't RTFM. As it happened in the past.
+
+The actual **major** pain point was indeed the last server.
+I've been accumulating various questionable packages on this one,
+for some reason, I installed ffmpeg in the past, which means there were
+lot of X-related libraries pulled in. During the cleanup, I unwisely
+must've fired off some purge command[1]… Which I acknowledged without
+looking properly. The result was that my entire /etc/letsencrypt
+directory was erased, as I used the distro-supplied certbot in the past.
+I just removed the package at some point and installed certbot via pip.
+So Debian/dpkg still thought that directory needed cleanup. Ooops.
+So I spent yesterday evening, extremely frustrated, fiddling with the
+nginx config manually, adding temporary fake certs/keys, so that nginx
+would start at all, so that certbot could work, and I could re-add
+the certificates again.
+
+Lesson learned: Read the fucking output before you hit enter.
+
+[1]: Via ansible, nonetheless.