this post was submitted on 13 Jan 2026
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Linux
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Linux is a family of open source Unix-like operating systems based on the Linux kernel, an operating system kernel first released on September 17, 1991 by Linus Torvalds. Linux is typically packaged in a Linux distribution (or distro for short).
Distributions include the Linux kernel and supporting system software and libraries, many of which are provided by the GNU Project. Many Linux distributions use the word "Linux" in their name, but the Free Software Foundation uses the name GNU/Linux to emphasize the importance of GNU software, causing some controversy.
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I don't think I've ever had a debian major upgrade go well. always easier to reinstall, but the stakes are so low on my own devices
Do you follow the step-by-step docs or just yolo it?
You should be proud of yourself. I've never seen dist-upgrade go wrong since woody - and I've upgraded quite a few machines. Did you ever bother reading the release notes for a new major version?
I'm a happy middleground. I've had two upgrades blow up on me, out of the tens I've done.
One was a usrmerge catch-22. It wouldn't let me install the package during upgrade, but also wouldn't let me complete the upgrade without the merger finishing. Ended up reverting the install and running the merge prior to upgrade.
The second failure was just... I have no idea what I did wrong. Some commands stopped working. Then I lost SSH. Then it wouldn't even boot. I had to do a full reinstall and rebuild. Not happy times.
Overall, it was just enough failure that I routinely run two backups prior to upgrades now. hahaha
I had some friction with Jessie to stretch and a little again from bookworm to Trixie. Nothing I couldn't solve, but there are still a few edge cases that aren't handled.
Funny that's how my Slackware upgrades always went, but I've had a great experience with Debian every time.