Session
Penetration Testing for Systems and Network Admins
The objective of this Capture-the-Flag style class is to take students with existing networks or systems administration experience and teach them how to:
1. Perform a comprehensive penetration test against Active Directory environments.
2. Spot a bad penetration test.
We understand that not everyone taking a pen test class will want to be a penetration tester. Hence, we have organized this class to be a well-rounded experience, allowing both aspiring red teamers and blue teamers to get the most out of it. This class will provide students with hands-on experience with all phases of a penetration test, from information gathering to reporting.
Students will need to bring their own laptop with Kali Linux installed and will be provided VPN access to a lab environment for a full week.
Instructions for participants:
The class VM image can be downloaded here: https://box.bluebastion.net/index.php/s/TQFN3dQYzLJiJsp
It is Kali Linux VM built for VirtualBox.
Please download and configure this ASAP. It is a large image (11.5GB) and can take a few hours to download.
If you’re not familiar with VirtualBox, use the following link for instructions on how to import an OVA: https://docs.oracle.com/cd/E26217_01/E26796/html/qs-import-vm.html
If you'd like to use your own Kali Linux VM, please ensure it has the following tools installed and pre-configured:
- Proxcychains
- Crackmapexec,
- Impacket framework
- Bloodhound and Python-Bloodhound ingestion script
- John the Ripper (Hashcat if you prefer and have GPU)
- Evil-WinRM
VPN Profile, lab manual, and slide deck will be made available during class.
Just a reminder, this is not an entry-level IT/Tech class. Penetration testing is a specialization within technology fields. You are expected to be comfortable with Linux and Windows to do well in this class. We will be using Kali Linux as our primary attack platform. You will be navigating the filesystem using command line, installing software using apt-get and Python-pip, cloning GitHub repositories using git, etc. On the Windows side, you will be attacking an Active Directory environment and exploiting configurations, not missing patches. So, it will help to be familiar with Active Directory user and device management. Should you need some resources to help you prepare, please let me know and I will be happy to recommend them.
I generally find https://tryhackme.com/ has useful resources around preparing for a penetration testing class or role. I specifically like the following:
- https://tryhackme.com/path/outline/presecurity Sections 2 (Networking Fundamentals), 3 (How the Web Works), 4 (Linux Fundamentals), and 5 (Windows Fundamentals)
- https://tryhackme.com/room/activedirectorybasics
Qasim Ijaz
Cybersecurity leader and educator
Rochester, New York, United States
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