• Georgia Institute Of Technology

• CS 6262

CS 6263 Network Security Page 1 Pen Testing Project

Table of Contents

Project 1: Introduction to Penetration Testing............................................................... 2

Introduction............................................................................................................................ 3

Learning Goals ....................................................................................................................... 3

Virtual Machine ..................................................................................................................... 4

Minimum Hardware to Run the Project 1 VM:....................................................... 4

Networks ................................................................................................................................ 5

Networking in Docker...................................................................................................... 6

Environment Setup:.............................................................................................................. 6

Project Tasks (100 points):.................................................................................................. 7

Setup ................................................................................................................................... 7

Task 1: Network Scanning (10 points).......................................................................... 9

Task 2: Exploit the Shellshock Vulnerability (20 points) .........................................10

Task 3: Brute Force with Metasploit (20 points)......................................................11

Introduction to Metasploit........................................................................................12

Task 4: Privilege Escalation (20 points) ......................................................................18

Task 5: Password Cracking (30 points).......................................................................19

Background on Using John the Ripper...................................................................19

Task 5.0 Demonstration of John the Ripper – Not For Credit..........................19

Overview of Tasks 5.1 and 5.2 ................................................................................20

Part 1: Cracking task51.zip .......................................................................................21

Part 2: Cracking task52.gpg......................................................................................21

Rubric ....................................................................................................................................23

Extra Task 6 – Optional, Not for Credit .........................................................................24

Task 6 Bypass Authentication with HTTP Request Smuggling .............................24

Submission:...........................................................................................................................25

Reminders:............................................................................................................................27

Acknowledgments: .............................................................................................................27

Appendix 1 – Resources / Links.......................................................................................27

CS 6263 Network Security Page 2 Pen Testing Project

Appendix 2 - Running the VM on an ARM-based Mac...............................................28

Emulating x86/x64 on Apple MX Chipset.................................................................29

Disclaimers...................................................................................................................29

Requirements...............................................................................................................29

Obtaining the Virtual Disk Image from the OVA .................................................30

Creating the Emulated Virtual Machine.................................................................30

Configuring the Emulated Virtual Machine...........................................................31

Completing Course Projects via SSH......................................................................31

Obtaining the VM's IP address.................................................................................31

Completing Project 1 over SSH ...............................................................................32

Appendix 3 - VirtualBox Networking..............................................................................32

NAT Networking.........................................................................................................32

Bridged Networking...................................................................................................33

Restarting VM Networking.......................................................................................34

Forwarding Ports to Your Host................................................................................34

Appendix 4 – VM Troubleshooting.................................................................................36

Closing...................................................................................................................................38

Project 1: Introduction to Penetration Testing

Summer 2025

Security Warning

This project involves port scanning and the programmatic creation of network attacks and other hacking techniques. Be certain that you always direct attacks at the Docker container ONLY. Accidentally scanning outside your local network could have serious consequences. The Docker network is on 172.22.0.0/24 (CIDR notation) in the VM, do not scan other networks!

CS 6263 Network Security Page 3 Pen Testing Project

- We make such warnings here, in part, so that you avoid unauthorized port scanning. It’s an interesting subject, you can learn more at https://nmap.org/book/legal-issues.html.

- These attacks are intended only for the isolated environment of the virtual machine.

- Your ISP Terms of Service likely ban unauthorized (or any) port scanning, don’t port scan the Internet.

- Never scan a computer that you don’t have explicit, written permission to scan.

Introduction

Penetration testing is an important part of ensuring the security of a system. This project introduces some of the common tools used in penetration testing, while also exploring common vulnerabilities (such as Shellshock and bit exploits). In this project, you will gain hands-on experience by exploiting a server running inside a Docker container, hosted within a virtual machine (VM). You will better understand the Shellshock vulnerability, how privilege escalation can occur, and how to crack weak passwords — all crucial elements in penetration testing.

On September 24, 2014, a severe vulnerability in Bash, nicknamed Shellshock, was identified. This vulnerability could exploit many systems at the time. In this project, you will gain a better understanding of the Shellshock vulnerability by exploiting it to attack a machine. The objective of this project is to get first-hand experience on this interesting attack, understand how it works, and think about the lessons that we can get out of this attack.

There are Tasks centering on the use of Metasploit and getting a privileged shell on the Docker container. There is also a new optional task, Task 6 HTTP Smuggling, that we hope students will try, but is not part of the graded project.

Learning Goals

In this project, you will:

• Learn to use penetration testing apps and techniques in a Linux

virtual machine, attacking a vulnerable Docker container.

• Perform network reconnaissance to discover open services running

inside a containerized environment.