Asklemmy

my first was windows for workgroups 3.11 with msdos 6.22 back in 1994; later upgraded to windows 95.

my first linux as mandrake linux (aka mandriva) in 2002 on kernel 2. i use linux fulltime now and no longer own a windows computer.

Knoppix 3.something

It was ages ago.

Comodore 64 os in the late 80's then msdos, win 3.1, etc. First Linux distro i believe was either slackware or debian.

Ubuntu Feisty Fawn. 2007. I was looking for new and exotic ways to avoid writing papers.

First operating system was DOS 4 or 5, I think. On big 5.25” floppy disks on an 8088. Unless we’re counting whatever was running on a commodore vic20.

My first Linux distribution was Red hat Linux, somewhere around 1997, 1998 and I had a really tough time getting it installed.

I also once had a trial version of os/2 warp. Which was fun but pointless.

Windows 95, Knoppix and Mandrake Linux.

DOS/Win3.1 I was pretty young. It was far back enough that it was still common to find Apple II's in my grade-school classrooms off to the side for when we had downtime. I regret that I was just a little too young to experience the Commodore 64 craze.

First OS was Windows XP and first Linux distro was Raspbian (now Raspberry Pi OS), but on my main computer the first distro I used regularly was Ubuntu

Windows 3.11

First OS was C64's Commodore KERNAL/BASIC 2.0 GEOS, if that even counts as an OS, the next was Amiga 500's AmigaOS

First Linux distro was Fedora

Sinclair Basic on my ZX81 with 1k ram. My first personal linux distro was Redhat 5.2. I used VAXVMS at work.

Amiga Workbench 1.3. - preemptive multitasking ftw

DOS s.u.s.e. 4.x or 5.x

MS-DOS 5 or 6. I guess technically I used whatever Apple IIes had, first, but really I just loaded games from disk.

DOS. Not sure what version, I was far too young to care. But not so young I couldn’t learn how to operate a command line interface!

Whatever an Apple IIe ran. Some sort of DOS from what I remember.

In high school I got my hands on an old Sun workstation with Solaris, and eventually after a week or so of compiling switched to Gentoo

If you could call it an OS, ZX spectrum basic was my first. My first Linux was Slackware 6 or 7 installed from a string of floppies. Good times.

C64 -> MS-DOS 3 -> 4DOS -> Win 95 -> Win 2000 -> Debian -> Ubuntu -> chaotic smattering of various distros that changed almost weekly -> Mint -> Arch -> Manjaro -> MXLinux -> SteamOS (SteamDeck), Rasbian.

My desktop OS history:

1. Windows 98
2. Windows XP
3. Windows Vista
4. Windows 7
5. Ubuntu
6. Linux Mint
7. Antergos
8. Arch Linux
9. NixOS

I've used others, but not enough to warrant a place in the list above.

Macintosh System 7. Then I moved to Windows 98, which was the style at the time.

Technically (but only very technically as we basically never used them and they were obsolete at the time already) it would have been a version of Acorn MOS but realistically it was Windows 3.1.

My first OS was most likely DR DOS 3.41

For my daily driver desktop PCs that was followed by

• MS-DOS 5.0
• Windows 3.11
• Windows 98 SE
• Windows XP
• Windows 7
• Windows 10

On the linux side, I got started with Gentoo, experimented with several lightweight distributions for an old laptop and had a Mint VM for a few years. These days I run Ubuntu on a couple of servers and in WSL. Never got around to using it as my main desktop OS.

For university I had (in order) an iBook G3, a MacBook and a MacBook Pro, so you can add most of macOS 10.x to that list.

TOS

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 was DOS (I think) on an Apple IIE at school. I think there were a few Commodore 64’s there as well. A couple years later we got our first home computer running Windows 95. Good times playing Doom, Jane’s Apache, an MS Flight Simulator.

My first personal computer was running Windows XP and I switched to Ubuntu sometime in 2004. Ran Ubuntu for the most part till a few months ago when I switched my desktop and laptop to NixOS.

Started self hosting services in 2012 and started with Ubuntu as base OS. Now though most of my servers are Proxmox with the VMs usually running Ubuntu LTS, though NixOS is starting to creep in there as well.

MS DOS 2.11.

For Linux I started with Wubi to install Ubuntu 8.04 Hardy Heron. It installed Linux as a program in Windows and added some kind of hacky boot entry to boot into Ubuntu from your windows partition. Pretty cool, and I'm still pretty nostalgic for the GNOME 2 aesthetic with compiz effects from that time.

First OS: TRSDOS 1.3

First Linux distro: Slackware 4

MSX, some version of MS-DOS, DR-DOS, Windows 3.0, 3.11, Slackware 3.0, Windows 95,98,NT,XP,7, CentOS, and now, MacOS.

At work, Windows XP,7 and 10, and several versions and flavors of RHEL.

Commodore64 for first OS, taught myself to type and then taught myself BASIC on that beast.

I honestly do not know what my first Linus distro was, whatever was on the machines in the CS half of the computer lab in college. First one I installed myself was Ubuntu, but I abandoned it almost immediately in favor of another distro that I also don't remember.

Probably some version of DOS, I can't remember. First Linux distro was Fedora Core 4.

Well, this sets a new level of recent here judging by the comments.

Desktop OS: Linux Mint 20 MATE. Yep, that's right. I only got my first proper computer in 2020.
Thankfully, I had to install the OS myself, which was of course preceded by choosing an OS.
I had Windows 10 on that laptop for 2 days which served me to compare different OSs and burn the install DVD. I had no flash drives, and just dug out one old DVD-RW. OK, I'll be honest, hearing about Linux first I was searching for "just Linux", pure Linux, not derivatives. Oh well, GNU+Linux copypasta actually being helpful.

Alright, but why did I "have" to install an OS if I got it with Windows? It was used. I did reset it, but even though it was my first proper PC, I had no lack of paranoia. I thought that someone before me could have put spyware on that.
And I was right. Not the way I thought, but I was. That someone was Microsoft.

First OS - DOS 5.0 First Linux - Knoppix

My first OS was Windows 98.

Linux distro was Ubuntu 6.0.

First social media post that's ever made me feel young! Earliest I remember was Windows 95, but I didn't do much besides play with MS Paint.

First OS: MS-DOS 5

First Linux (many years later): Yellow Dog on one of those dome-shaped iMacs with the PPC chips

It was a Lisa. Those were good times.