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Part 1 – Setup & Experiment

Use at your own risk. This experiment runs penetration testing tools in a self-contained local lab environment against an intentionally vulnerable application. Never run these tools against systems you don’t own or have explicit written permission to test. Your system, your responsibility.

This part covers the full setup and the experiment itself — from a blank OrbStack install to Goose running live pentesting tools inside Kali Linux against OWASP JuiceShop.

Requirements

Step 1 – Deploy JuiceShop as a Docker container

JuiceShop runs as a Docker container. In OrbStack, containers and VMs share the same internal network, so the Kali VM will be able to reach JuiceShop directly by IP.

Open a terminal on your Mac and start JuiceShop:

docker run -d \
  --name juiceshop \
  --restart unless-stopped \
  -p 3000:3000 \
  bkimminich/juice-shop

Verify it’s running:

docker ps | grep juiceshop

Find the container’s internal IP (you’ll need this from Kali):

docker inspect juiceshop | grep '"IPAddress"'

Note this IP — it will typically be something like 198.19.249.x in OrbStack’s default network. You can also access it from your Mac at http://localhost:3000 to confirm it loaded.

Step 2 – Create a Kali Linux VM in OrbStack

OrbStack supports Linux VMs directly. Kali is available as a pre-built image.

Open OrbStack, go to Virtual Machines, and click New Machine. Select Kali Linux from the distribution list. Give it a name (e.g. kali-pentest), allocate at least 4 CPU cores and 4 GB RAM, then click Create.

Once running, open a shell into the VM:

orbctl ssh kali-pentest

Or click the terminal button directly in the OrbStack UI.

Step 3 – Install pentesting tools in Kali

Kali’s default image includes many tools, but it’s worth confirming the ones Goose will use are present:

sudo apt update && sudo apt install -y \
  nmap \
  nikto \
  sqlmap \
  gobuster \
  hydra \
  curl \
  ffuf \
  wordlists

Verify you can reach JuiceShop from inside the VM (replace with your actual IP):

curl -s -o /dev/null -w "%{http_code}" http://198.19.249.x:3000

You should get 200. If not, double-check the container IP and that JuiceShop is running.

Step 4 – Install and configure Goose inside Kali

Install Goose inside the Kali VM:

curl -fsSL https://github.com/block/goose/releases/latest/download/install.sh | bash

Configure Goose to use either a local model or Claude API. For Claude API (recommended for reliability):

goose configure

Select your provider and paste in your API key when prompted. Goose stores config at ~/.config/goose/.

Enable the shell extension so Goose can run commands:

goose configure extensions

Enable Shell (also called computer or bash depending on version). This is what allows Goose to actually execute nmap, sqlmap, and other tools rather than just describing how to use them.

Step 5 – The experiment

With everything in place, this is the prompt used to kick off the experiment:

You are a penetration tester conducting an authorised security assessment of a web application 
running at http://198.19.249.x:3000. This is OWASP JuiceShop, an intentionally vulnerable 
application set up specifically for this test.

Your task:
1. Perform reconnaissance and identify the attack surface
2. Scan for open ports and services
3. Enumerate the web application for vulnerabilities
4. Attempt to exploit any findings you discover
5. Document everything you do and what you find

Start with passive recon and work your way toward active exploitation. 
Think like a pentester, not a scanner.

What actually happened

(This section will be filled in after the experiment runs — check back soon.)

What follows is an honest account of the session — what Goose ran, what it found, where it needed help, and what it missed entirely.

Recon and scanning

Web enumeration

Exploitation attempts

Where Goose needed help

What it missed

Observations

(To be filled in after the experiment.)

What’s next

This was a first pass with a general prompt and default tooling. Possible follow-ups:

  • Give Goose a more structured methodology (OWASP Testing Guide phases)
  • Try a different local model and compare behavior
  • Attempt a more targeted attack with human-guided pivoting
  • Document specific JuiceShop challenges solved vs. unsolved

Related guides