What was your very first operating system?

Let’s take a quick trip down memory lane. What was the first OS you ever used, and what was the first one you actually used for programming?

My first introduction to computers was Windows 98, mostly playing pixelated games and messing up the desktop settings. But the first OS where I actually opened a terminal and wrote code was Window 10.

Drop yours below. I’m curious to see the demographic split here between the MS-DOS veterans and the MacOS natives.

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Windows XP was probably the first one I properly remember using. The startup sound, blue taskbar, slow boot, and random desktop shortcuts still feel nostalgic. It was messy, but it made a lot of us curious about computers.

The absolute king of nostalgia.

Windows 98. I still remember the desktop maze screensaver and the pure panic of hearing the dial-up internet connection sound when I clicked something by accident. What a time to be alive.

Windows 98 veterans unite! The panic of accidentally launching the internet dialer was real. It’s wild to think how far we’ve come from those pixelated desktop days to where we are now. Thanks for taking a trip down memory lane!

I guess I bridge the gap a bit. First OS ever used was Windows 98, and I vividly remember the panic of accidentally deleting desktop shortcuts thinking I had broken the whole computer. But the first OS I used for serious programming was a lightweight flavor of Linux called Mint, running on a completely underpowered netbook. It taught me everything I know about resource management and command-line basics.

That shortcut panic is a universal core memory for anyone who grew up in that era. Transitioning from Windows 98 to Linux Mint on an underpowered netbook is an elite progression, though. Nothing forces you to master the command line, optimize configuration files, and respect memory limits quite like trying to squeeze development performance out of limited hardware.

My first operating system was Windows 2000 on a clunky family desktop, but Windows 10 was where I actually wrote my first line of code too. I started out with the Windows Subsystem for Linux (WSL) when it first dropped, which gave me the best of both worlds—the comfort of Windows for daily use, but a real Linux terminal for compiling code and running web servers.

Windows 2000 was such a workhorse of an OS. Starting your development journey right when WSL dropped was perfect timing, though. It completely shifted the landscape by removing the old friction of dual-booting or running heavy virtual machines. Getting that native Linux environment alongside a familiar desktop environment was a massive quality-of-life win for developers starting out.

Windows 7 was my gateway to computers, mostly for schoolwork and browsing the web. But my coding journey didn't start until I got my hands on a MacBook Pro running macOS High Sierra in college. The fact that macOS had a Unix-based terminal built right in made setting up my local development environment for web development so much smoother than trying to wrestle with Windows paths at the time.

Windows 7 was arguably one of Microsoft's best, but moving to macOS High Sierra for development makes total sense. Having a native Unix environment right out of the box without dealing with environment variable paths, Cygwin, or third-party terminal emulators was a massive competitive advantage for macOS during that era of web development. It just let you focus on the code instead of the tooling.

I fall squarely into the MS-DOS camp on this one. My very first OS experience was booting up an old IBM clone using floppy disks and typing cd/games to launch whatever pixelated platformer I could get my hands on. Fast forward a few years, and my first programming environment was Turbo C++ running on Windows 95. There was something incredibly satisfying about that classic blue editor screen.

Booting from a floppy disk and navigating via cd/games is the definitive classic experience. Moving from raw DOS commands to the Turbo C++ blue screen on Windows 95 is a legendary starting point. There was no stack overflow or auto-complete back then—just you, the compiler errors, and whatever physical programming manuals you could find.

This brings back some great memories. My first introduction to computing was Windows XP, which will always hold a special place in my heart for that iconic wallpaper and the hours spent playing Pinball. But the first OS where I actually started programming was Ubuntu Linux. I accidentally broke my Windows partition trying to dual-boot it, which forced me to learn the terminal and write my first Python scripts out of sheer survival.

Accidentally wiping out a Windows partition while attempting a Linux dual-boot is practically a rite of passage for software engineers. There is no better motivator to master the Linux terminal and bash scripting than realizing you just nuked your primary operating system and have to figure out how to make things work out of sheer necessity.

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What was your very first operating system?

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What was your very first operating system?

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