Tryhackme Junior Pentester Path: Setting up dirb with WSL

Rameen Rizwan — Tue, 27 Oct 2026 08:48:45 +0000

I'm currently working through the Junior Penetration Tester path on TryHackMe, and I hit an immediate wall on the very first room: Offensive Security Info.

The room expects you to run Linux tools like dirb from your own machine. If you're on Linux, great — you're done. But if you're on Windows, there's no built-in way to run these commands.

This guide is exactly what I wish existed when I started: a step-by-step way to get a real Linux terminal on Windows so you can follow along in real time.

Prerequisite: Windows 10 or 11. No dual-boot, no VM, no extra downloads needed.

Step 1: Install WSL (Windows Subsystem for Linux)
WSL lets you run a full Linux kernel inside Windows — no rebooting into another OS, no VirtualBox.

Press the Windows key, type PowerShell.
Right-click → Run as administrator.
Run:

wsl --install

Wait for it to finish, then restart your computer when prompted.

Step 2: Choose and Install a Linux Distribution
After restarting, open PowerShell as admin again.

List what's available:

wsl --list --online

You'll see options like Ubuntu, Debian, and Kali. For pentesting, Ubuntu is a solid default (and Kali is available too if you want the full toolkit later).

Install your pick:

wsl --install Ubuntu-24.04

On completion, a terminal window opens asking you to create a username and password. This is your Linux sudo account — it doesn't need to match your Windows credentials.

Step 3: Install dirb
Open your new Linux terminal — either from PowerShell by typing ubuntu, or by pressing the Windows key and launching the Ubuntu app directly.

Then:

sudo apt update
sudo apt install dirb -y

Step 4: Verify It Works

dirb http://example.com

If you see a list of discovered directories and files, you're fully set up. 🎉

Now head back to the TryHackMe room and run the same command against the target IP provided in Task 3.

A Note on the Rest of the Room
Once your environment works, the room itself is straightforward:

Tasks 1–2 are intro reading and simple questions.
Task 3 is where dirb does the heavy lifting — point it at the target and read the output.

Wrapping Up
Setting up WSL takes about ten minutes and removes the single biggest friction point for Windows users starting in offensive security. Every future room in the Junior Pentester path gets easier from here.

If this saved you some frustration, drop a 👍 — and follow along as I work through more of the path.

DEV Community: Rameen Rizwan

Tryhackme Junior Pentester Path: Setting up dirb with WSL