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Have you ever done an Active Directory machine on TryHackMe, HackTheBox, Pentester Academy, or any other platform and thought, “Huh, that was really fun!”?

Well, I certainly have. One of Penetration Testing’s most interesting topics (to me) is Active Directory. New security flaws are being discovered every day, this makes it incredibly useful to have an environment on-hand already built out. To do this, you’re going to need several things on hand, let’s go over them real quick:

Windows Server/Client ISO

These are relatively easy to acquire, you can do so with the Microsoft Evaluation Center. This can be found at the following URL:

https://www.microsoft.com/en-us/evalcenter/

At the time of writing, you can download either Windows 10 or 11, or Server 2019 or 2022. These are completely free to download, and have a trial range between 180 and 90 days. However, it is possible to extend this trial with the slmgr /rearm command. This is a general reminder – these devices are not designed to be used in a production environment. It is highly recommended that you download Server 20XX first. Setting up an Active Directory Environment is generally the same across all Windows Server versions. For the purpose of this post, I will be using Windows 10 and Server 2019.

Virtualization Software

This is another key thing that you should have – It is not required, you can use real metal, but this will take a considerably amount of time. I will personally be using VMWare Workstation, but just about any virtualization software will work as long as you can add VMs into an isolated network.

I have done this by creating a “NAT” network in the 10.10.10.0/24 Subnet with a Default Gateway of 10.10.10.2.

https://s3-us-west-2.amazonaws.com/secure.notion-static.com/ef03cc2b-5cbc-47c1-9c91-e7b241fb6e68/Pasted20image2020211105204953.png

I have went ahead and disabled DHCP, this is because DHCP will be handeld by Active Directory Sites and Services. We will go into this in detail a little bit later.

Organization

This is arguably the most important thing; having an Active Directory environment is good, but if you can’t remember the credentials for anything, can’t remember the IP Addresses, or don’t remember your chosen naming scheme, you’re gonna have a bad time. I highly recommend keeping credentials for your Lab environment in someplace like a KeyPass vault or a Spreadsheet.

Installing Windows Server