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InsiderJob is a multi-machine Capture The Flag (CTF) experience built entirely with Docker and Flask, simulating a compromised internal development environment where trust is the greatest vulnerability.

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Warning

🚧 Work in Progress
The CTF is still under development. Machines 4 and 5 are coming soon, along with the final web-based flag submission interface.

InsiderJob CTF — "Infragon Compromised"

🎯 Objective

You are E., a disgruntled developer inside Infragon Systems. After repeated security concerns were dismissed by upper management, you've decided to turn their negligence against them.

This Capture The Flag (CTF) simulates your journey through 5 interconnected Linux systems. Each container represents a real machine in the network. Your mission: move laterally, escalate privileges, and capture the root flags.

Flag format: coops{...}


🖥️ Machines

Machine Role Status
DevMachine01 Developer sandbox ✅ Complete
RepoServer Internal Git sync server ✅ Complete
QABox QA runner node (jump box) ✅ Complete
JenkinsCI CI pipeline system 🚧 Coming Soon
AdminBox Core infrastructure admin node 🚧 Coming Soon

Each machine is exploitable from the previous one — follow the narrative and use clues to move forward.


Setup Instructions

  1. Clone the Repository
git clone https://github.com/dcooper94/InsiderJob
cd InsiderJob

Build & Launch the Environment

docker compose build
docker compose up -d

Interact with Machines

For machines with restricted shell access (like DevMachine01), use:

docker exec -u devuser -it devmachine01 bash

🔄 Resetting the Environment

To clean and rebuild everything:

./reset.sh

This script removes Docker volumes and containers and resets persistent state (like Git repos or logs).

Notes

No external internet access is required.

Flags are generated at runtime inside each container.
Tools like ping, ip, netstat, cron, git, ssh, and python3 are installed where relevant.

A Flask-based logger and web front-end for flag submission is planned for final release.

Good luck. You've warned them long enough. Now it's time they listened — the hard way.

About

InsiderJob is a multi-machine Capture The Flag (CTF) experience built entirely with Docker and Flask, simulating a compromised internal development environment where trust is the greatest vulnerability.

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