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.
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DOS -> win95 -> win98 -> debian (and i'm still here 24 years later...)
Sinclair Basic on my ZX81 with 1k ram. My first personal linux distro was Redhat 5.2. I used VAXVMS at work.
Briefly some form of DOS on an Amstrad PC when I was very young, then Windows 95
My first Linux was a few years later with Mandrake IIRC, which I dual booted with Windows 98SE
Been running combinations of Linux and windows since then, with MacOS getting involved in the 2010's too
Whatever Commodore 64 ran, back when I was a little kid in the early 90s.
Windows XP
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.
Knoppix 3.something
It was ages ago.
PC-DOS on an IBM 5150 (iirc).
Windows 95, Knoppix and Mandrake Linux.
Hmmmm Amsdos on an early amstrad CPC machine
First I put real time on would have been the Atari TOS, man those machines where the biz at the time!!
Windows 3.11 and Kubuntu 6.06LTS (still have the CD!)
Ubuntu Feisty Fawn. 2007. I was looking for new and exotic ways to avoid writing papers.
Windows 3.11
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
DOS s.u.s.e. 4.x or 5.x
Whatever an Apple IIe ran. Some sort of DOS from what I remember.
Desktop: Windows XP
Linux: Probably Raspbian on a Pi 2 b
Tech has come a long way since then lol
My first OS was Apple OS and what the NCR's ran in 1978. My favorite game was snipes on Netware in 1986? My first OS distribution via retail box was windows 1.0. My first Linux distribution was FreeBSD 2.0 er wait.... My first Linux distribution was Debian 1.1 buzz on 3/5" floppies.
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.
MS DOS v4.somthing. (1995)
Slackware that came on three 5.25" floppies. (1997)
First hard drive Linux: Debian.
Eventually red hat for several years, then back to Debian based (mint etc) around 2005. Been using Sid (Debian "unstable") for a long time.
Comodore 64 os in the late 80's then msdos, win 3.1, etc. First Linux distro i believe was either slackware or debian.
First operating system was DOS 4 or 5, I think. On big 5.25β floppy disks on an 8088. Unless weβre 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.
The first OS I recall using is Windows 7 (yes Iβm young), and for Linux, I switched from Windows 11 to Linux Mint, which is what I use in the present day.

First OSish was what came default with the Commodore 64. My first full fledged OS was Windows 3.11. My first Linux distro was Mandrake I think 6.
Commodore ROM BASIC; 1980
First OS on a computer I personally owned? Windows 98. First Linux distro was Source Mage.
If not counting ownership, then Apple IIs at school and then slightly later my family got an Amstrad that was primarily a DOS machine, but could also boot (by switching floppies several times) to some sort of GUI.
Le menu.
On the Linux side: Crunchbang Linux when it was running Debian
I tried Microsoft Windows & Apple OS X before that, but that is is now behind me⦠as is Debian & Arch being a NixOS user for the last few years.
Microsoft Extended BASIC
First OS windows 95 First linux distro ubuntu Currently manjaro, windows 11, macos
My first OS was whatever ran on a Commodore 64. I guess the Commodore kernel and Basic?
My first distro was whatever version of Fedora was current in the fall of 2008. I'd gone to university that year and my laptop crapped out. Couldn't afford a legit Windows license at the time to replace it, and I'm pretty sure I just remembered that Red Hat was a thing and found Fedora that way. One thumb drive and 16 years later, still using linux, so I guess that was about the only good thing to come from my abortive first attempt at higher education.
On my first PC it was DOS 2.0, but before that I had a Vic-20, then a Commodore 64.
Windows 7 -> Windows 10 -> Kubuntu -> Linux Mint -> Nobara -> Pop!_OS -> OpenSUSE TumbleWeed -> EndeavourOS
DOS - Win3.1 - Win95/98 - BeOS - Red Hat Linux - WinXP - Mac OS X - WinVista/7/8 - MacOS X - Win10 - Debian Linux (and staying with it).
The first one I remember using was good old Windows 98.
Mac OS 7. By the mid-2000s, I adopted Arch Linux after looking into some other Linux distributions.
Reading the comments I want to say I feel old (25y) but compared to others I feel like a gen alpha
I came late in the tech world. I started with Windows XP
And my first distro was Ubuntu 10.10 till Ubuntu 17.10. Now I just hop from distro to distro. Right now using Pop!_OS for a year now.