WSL and Debian: A Lesson in Patience (and Mild Suffering)

 

Windows Subsystem for Linux (WSL) is one of those things that sounds amazing on paper. The idea of running a full Linux environment within Windows—no dual-booting, no clunky virtual machines, just a seamless terminal—seems almost too good to be true. And depending on which distro you’re using, it almost is.

But of course, I wanted Debian. Because of course, I did.

WSL: Great in Theory, Frustrating in Practice

Setting up WSL itself is easy—just a simple command in PowerShell, enable a few features, and you’re good to go. But as soon as I veered off the beaten path (read: not Ubuntu), things started getting... annoying.

First off, Debian on WSL isn’t quite the same as Debian on bare metal. The moment I tried doing anything remotely system-level, I ran into odd limitations. Systemd? Not enabled by default. Want to run background services like a normal Linux system? Have fun manually configuring workarounds. Want full compatibility with certain networking tools? WSL does some strange things under the hood that can make them behave in unexpected ways.

And let’s talk about file paths. Mixing Windows and Linux filesystems is technically possible in WSL, but it always feels like you’re not supposed to do it. You can access Windows files from WSL and vice versa, but permissions and ownership get messy fast. It’s functional, but it’s far from seamless.

The "Why Am I Doing This?" Moment

At some point, while troubleshooting why a package install wasn’t working as expected (spoiler: WSL does some weird things with permissions), I had a moment of existential crisis. Why am I bending over backward to make this work when I could just SSH into a real Debian system?

And that’s the thing—WSL is fantastic for casual Linux tasks, but when you start expecting it to behave exactly like a native Linux install, you’re in for a reality check. The convenience is undeniable, but there’s always a catch.

So, Is It Worth It?

For quick access to a Linux shell on Windows? Absolutely. If you just need a terminal for scripting, development, or running Linux tools without the overhead of a VM, WSL is great.

But for anything serious? I’d rather spin up a dedicated Linux machine. Or at the very least, stick with a distro that plays more nicely with WSL.

And yet, here I am, still stubbornly trying to make Debian work in WSL. Because some things never change.