Debian Upgrade Marathon: 3.1 Sarge
Posted4 months agoActive4 months ago
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The post documents the author's Debian upgrade marathon from version 3.1 Sarge, sparking a discussion about the pros and cons of upgrading versus reinstalling and the reliability of Debian's upgrade process.
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Sep 12, 2025 at 4:55 PM EDT
4 months ago
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Sep 15, 2025 at 8:18 PM EDT
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Sep 16, 2025 at 4:39 PM EDT
4 months ago
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ID: 45226657Type: storyLast synced: 11/20/2025, 3:44:06 PM
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It can be good for workstation laptops, and for pets-not-cattle servers.
Stability for a couple years, then in-place upgrade to newer versions of things all at once. Whenever the timing is good for you (because you can keep using `oldstable` for a long time, with security updates).
Whether this upgrading incrementally keeps working smoothly for decades, I haven't read all of OP's posts to find out. But I've had machines running well after a few major upgrades, and even moving the HDD/SSD between upgraded laptop hardware.
Also, I must be getting old, because in my mind systemd and Gnome 3 are still fresh controversies, not part of a “remember when” retrospective.
Yup! :-) In Debian, it was a decade ago (10 and 12 years respectively, in Jessie and Wheezy).
So you remember when /usr used to not be merged? Joking.
https://wiki.debian.org/AutomatedUpgrade
It's relatively deterministic too, I've used that combined with apt-offline to upgrade offline servers successfully.
I wish I had more stories to tell, but that’s the thing I like about Debian.
It's amazing that there are archives online for the old versions, or maybe it's just amazing to someone using FreeBSD which seems to drop old versions very quickly (when 13 was out the 11 repos were nowhere to be found).
also some very old repos went away over time, so your best bet is to always use the official debian repo, maybe with one extra containing software that should be on that server
with that said, it's one of the painless upgrades you can do
It's a great read but...
I run Debian since version 1.1 (not 11 but 1.1) or so (and I was using Slackware before that) and I always re-install my entire system from scratch. I never ever upgrade.
YMMV but to me if you upgrade if either the old (with all your configs) or the new version has a security exploit you are toast. While if you re-install from scratch, you're only toast if the latest version has a security exploit.
Also it helps to keep my skills sharp: I'm forced to re-install and re-configure everything and I like it. I use the opportunity to enhance my shell scripts, to learn new stuff, to do a few things here and there in a better way, etc. FWIW I'm not on Trixie yet (except on one NUC): I need to switch one of these days (and I won't upgrade).
Now the usual disclaimer... I don't claim my way to be the way: to each his own bad taste.