C64 Basic, Yggdrasil Linux. I wanted to install Minix, in the pre-Linux times, but it was beyond my abilities
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Atari 800 basic.
Gentoo was the first distro I used for any significant amount of time (college).
Windows 98. Later the first Linux distro I tried was Mandrake Linux but I didn't really get into it until later with Crunchbang.
My first OS was DOS 5.0, I switched to linux with Fedora core 6
I had a Debian PC for a while, it was more of a project. IT work still revolved around Windows back then. Later I discovered Puppy Linux and ran that on a live USB. I encrypted the hard drive in my work laptop and never had to worry about anything making from the USB to my work data. Not a bad way to live, only had to carry around one laptop when I traveled for work.
My first OS was Windows 98.
Linux distro was Ubuntu 6.0.
Amiga back when you booted off floppies.
Then I guess ms-dos for pc.
For Linux I got a box set for redhat from compusa in 99 and learned from there.
First OS - DOS 5.0 First Linux - Knoppix
Red Hat 7
mint->chromeOs->kali->windows->arch->openbsd->arch->nix