The insidious urge to fix what ain’t broke has arisen. I’ll probably follow the official documentation, unless someone has a better suggestion.
I’m not running anything unusual and I haven’t done much, if any, “customization”. I update packages maybe a couple of times a week, so they’re current.
Should I go ahead and put myself through this now, or wait until support is dropped and I’m forced?
0.076
Update when you can afford downtime. The update should be painless but you know how it is: things go crazy when they shouldn’t. Every time.
The upgrade itself is never a problem.
The real problem is when your server is running an old software that breaks after the update.
For example I had an old php/drupal site and it broke after upgrading debian because the upgrade also updated php to a newer version that is not supported by that old version of drupal.
This is where docker becomes a godsend
Most of my infra is Debian, and I did it without serious incident:
#Update everything to latest apt update && apt upgrade && apt full-upgrade && apt --purge autoremove reboot #Verify that debian_version is 12.x (STOP IF NOT 12!) cat /etc/debian_version #Check for any pinned or held packages apt list '?narrow(?installed, ?not(?origin(Debian)))' apt-mark showhold #Swap bookworm for trixie in repo files sed -i 's/bookworm/trixie/g' /etc/apt/sources.list sed -i 's/bookworm/trixie/g' /etc/apt/sources.list.d/* #Carry out update apt update apt upgrade --without-new-pkgs -y apt full-upgrade -y reboot #Verify that debian_version is 13.x cat /etc/debian_version #Modernize apt sources to v3 apt modernize-sources -yAnd then maybe apt update to make sure the updates still work OK.
Sometimes you have to make changes to certain repos that don’t have Trixie manifests, but that’s easy enough to roll back.
apt modernize-sources -y
Thanks for this - I hadn’t seen it yet in the docs I’ve been looking at.
No idea what it does, but it looks legit, so I’ll run it!Apt v3 comes with some quality-of-life stuff that apt has been direly missing for years, and one of those is apt sources that make sense to a human.
So the new apt source files have local key location, components, suites, and Uris.
The sources from the before-time just had a one-liner with a uri and some components.
Edit:also the modernize command makes a backup of the source files it touches.
The official docs have everything, though not as well ordered and concise as they could be.
I’ve taken my server from 11 to 12 to 13. Only issue was 11->12 where backports caused some issue that I no longer remember the specifics of (never broke SSH link), so I just don’t fuck with backports anymore. You need to have your shit together for backports, from what I’ve gathered.
12->13 was abs smooth as butter. Extra 3rd party repos weren’t even an issue. One I had to leave “bookworm” because they didn’t have trixie entries; I found it had no trixie entry by looking at the repo itself - it just kept working no problem after the upgrade anyway.
And I have a “stretch” repo I took from 12 to 13 on another server (it’s mongoDB 4.4 for unifi, an abs shitshow of software those bozos cook up)Anyway tldr docs are good narry a problem will occur.
For the most part, it’s pretty painless. Unless you have a super complex setup you’ll be fine.
I had no trouble at all.
I’ve found that dist upgrades themselves are fine, but it usually breaks something. Last time it was my janky WordPress installation which was using PHP 7.4. The wordpress version was up to date but it wouldn’t use the installed 8.2 php and just broke. In the end I installed a fresh wordpress and copied the data over.
The trick is to get wordpress from debian’s repos itself. That way your wordpress is managed by debian and receives automatic security updates.
I updated NAS, VPS and Raspberry Pis not so long ago. All when smooth and without issue.
Is it painful? I’ve upgraded several versions without difficulty. “third party” repositories are problematic so be sure you follow the guidelines about disabling them.
I recently upgraded my gaming pc from Bookworm to Trixie. It was fairly painless. Had to fiddle with some third party repos, but I anticipated that and read up on them beforehand.
I’ve yolo’d every major upgrade from debian 8 to 13 without any backups of configs and survived… (dont do that though)
For most desktop systems where you’re not dicking around with files in /etc, there is almost no pain ever
For servers, dealing with the “do you want to install the maintainers version of ____.conf”, sucks… trying to remember all the things i put in php.ini is a pain
Probably skill issue
This is why I’ve started running most services as containers inside of an LXC container in Proxmox
I’ve done it twice so far (main server and a Raspberry Pi). Although I recall I had some package breakage with the main server (some changes in Podman that did not go well with the migration to pasta, the new rootless network stack), the process was mostly pain free and I could fix things remotely with SSH.
I update my servers very promptly and have never had a problem with a version jump. Apt handles this well.
Just be careful if you use Dovecot MDA, as it’s configuration files format changed. There’s a nice guide on dovecot’s documentation covering this change.







