Is it Possible to Upgrade Debian 1.3 to Debian 11?

In this video, I take Debian 1.3--which came out back in 1997--and try to upgrade it all the way to Debian 11--the latest version at the time of making this video.

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[ENNEN]

The wall that looks like them compute chips my grandson is always talking about, the hackerman text scrolling in the background on his displays, the slight dimness in his room, the fact he has TWO screens and actually NEEDS the second one, talking about linux...

Guys... I'd better call the FBI because I think I found him... I found the hacker known as 4chan.

[jongeduard]

It's kind of possible! And I did it, from 5 upward. But how... Well, just gall me a geek. 😄

First I succeeded from 6 to 12 and then again from 5 to 12. And then further to 13 testing. One next version at a time, so that's 7 steps for the first time and 8 steps for the latter. And actually from completely 5 to 6 failed the first time for me too, so that's why I decided to start from 6, before eventually trying from 5 again.

And it was a LOT of work with a lot of times where I had to restore a previous VM image backup, but an real historic learning experience.
The main thing is that you need quite a lot of understanding of things going on. And you have to do a lot of research.
First everything from the archive mirrors, later from the still maintained version mirrors.

Most importantly you have to be super precise with what you put in the sources list file, and be aware of some structural changes that they made to the sources during the years.
Basically, as long as apt update gives errors, the sources list is still incorrect and you will end up with a broken result.
In many cases I needed several apt update attempts before I was ready to do the actual upgrade and dist upgrade.

Also an issue is that I faced a couple of problems like having to manually removing some packages in order to get the upgrade in anyway done.
And in the case of Jessie, the desktop did not work at all, including gdm, so really had work in a non graphical TTY. Which is not a real issue.

[DhavidSetiawanKilluaDhavid]

6:27 [I don't know about the old Debian, but I'm using Debian since Debian 5] I think you need to use "halt" command. Not "poweroff"

[eulondon]

Back in the day this was a big problem because the time between releases were too long. What one would do is keeping updating with the security updates. Before going to the next version, one would go to testing when RC was near. And back to release when and do a "fake" dist upgrade". Because most stuff was already RC. The gpg error is because of time expired so you should keep the vm time not too far from the usual dates one would be upgrading. And forget networking that would just mess with the dates again. The glibc you should take the source of the required version or similar version source and compile to get past the error. Dont worry my first debian was 3.0 but everyone was on testing because 3 stagnated before the community took action for them to change the way the "releases" work. Good old days.