Beginners Guide to Self-Learning Windows and Active Directory: Part 1
In 2018 I began a journey to learn Windows and Active Directory.
Interesting enough, I’ve noticed that most universities don’t require Windows Internals or Active Directory in their curriculums. This is peculiar to me considering the market share Microsoft has in IT infrastructure around the world. Moreover, on-premises Active Directory networks are not going away even with the large shift to cloud and hybrid infrastructures. So, in this post, I’m going to share the references I’ve used in self-learning Windows and Active Directory.
1. Open a Command Prompt and Look Around
The best way to learn where everything in a file system is to open a command prompt and look in every directory. Google what those directories usually hold and their use. Play around with different commands. Write some batch scripts for fun. Here are two of my favorite references for learning the command line:
2. Read Ned Pyle’s Post-Graduate Active Directory Studies
… and follow him on Twitter (@NerdPyle) for walkies and timeline cleanse worthy pictures. This will take a while so I hope you’re not in a hurry.
3. Build a Lab
You can read all day, but without hands on keyboard what are you really learning? Building a lab can seem intimidating and expensive. But you can do it reasonably inexpensive. Buying old servers on eBay is a great way to get the hardware you need for a low price. While they can be noisy and consume a lot of energy, they’re worth the $300–$500 you’ll spend.
You’re likely to buy a Dell Poweredge or HP Proliant if you go this route. It’s a great way to get enough RAM (64gb+) and hard drive space. It’s my suggestion to stay away from spindle discs if possible and go for solid state drives. You’ll want at least 1TB of drive space unless you already have a NAS. Also, 2 CPUs with at least 12 cores is best.
For those that have a bit more money to spend, you may opt for a Dell Optiplex with 64gb RAM and 1–2TB solid state drive. You might be able to find one without an operating system. In the current market, these specs will cost you $1500–2500. People, including myself, like the OptiPlex for it’s small form factor and minimal noise compared to servers.
Once your server comes, it won’t have an operating system. You’ll want to install ESXI or another hypervisor technology (i.e. Proxmox, Hyper-V). You can google how to install ESXI on a bare metal server.
Great. Now you’ll need some images to import into ESXI to build your lab.
You’ll want multiple images: Windows server 2008r2, 2012r2, 2016, 2019, 2022, and Windows 10 & 11 Enterprise. Once you get your first server up and running, promote it to a domain controller. Then, join other machines to the domain. Also, you may want to segment your lab from your home network instead of having a flat network. You can achieve this by using a PFSense firewall. Below is a nice guide to streamline this process (disregard Virtual Box section).
Advice: Don’t under provision your VMs. Windows can produce weird behaviors when under provisioned. For your DC, you’ll want at least 4gb RAM and 160gb hard drive space. For Exchange, you’ll need at least 8gb RAM. Workstations and member servers should get 4gb RAM. Also, ESXI will need about 100gb hard drive space.
4. Build Your Domain and Experiment with Server Roles/Group Policy
You’ll want to create a few OUs with users in various groups and experiment with different group policy settings. You’ll also want to set up various server roles: file server, web server, sql server, ADCS, Exchange, and maybe even ADFS.
5. Read ADSecurity.org
Sean Metcalf is an Active Directory expert and his blog is a must read.
Congratulations! After all this, you are now ready to really learn Windows and Active Directory. Above is a high level overview of pre-requisite knowledge required to delve deeper into Windows security and internals.
