Project Overview
[Enterprise 101]
Project Overview
Network Topologies
Base
NAT Network
- Name: project-x-nat (NatNetwork)
- IP Address Range: 10.0.0.0/24
o Usable Range: 10.0.0.1 – 10.0.0.254
o DHCP Dynamic Scope: 10.0.0.100 – 10.0.0.200
Attacker
Cyber Attack Simulation
Hosts
Hostname [project-x-…] IP Address Function
-dc (corp.project-x-dc.com) 10.0.0.5 Domain Controller (DNS,
DHCP, SSO)
email-svr 10.0.0.8 SMTP Relay Server
-sec-box 10.0.0.10 Dedicated Security Server
-sec-work 10.0.0.103 or (dynamic) Security Playground
-win-client 10.0.0.100 or (dynamic) Windows Workstation
-linux-client 10.0.0.101 or (dynamic) Linux Desktop Workstation
attacker dynamic Attacker Environment
Accounts & Passwords
Account Password Host
Administrator @Deeboodah1! …-dc
janed@linux-client @password123! …-linux-client
project-x-sec-work @password123! …-sec-work
sec-work@sec-box @password123! …-sec-box
email-svr@project-x-email-svr @password123! …-email-svr
attacker@attacker attacker attacker
Operating Systems
Windows Server 2025: Designed to support enterprise-level applications and network
management, and identity management. This will be used as the directory services server,
acting as the central hub for network connection.
Windows 11 Enterprise: Desktop operating system optimized for everyday productivity. Most
common operating system used in business environments for employees. This will be used to
simulate a business user.
Ubuntu Desktop 22.04: General-purpose desktop. Commonly used for software development.
This will be used to simulate an enterprise software development environment.
Security Onion: An open-source platform for security monitoring, log analysis, and intrusion
detection, used by cybersecurity professionals to detect, investigate, and respond to network
threats and incidents.
Ubuntu Server 2022: A Linux server operating system widely used for hosting applications,
databases, and web services. This will be used as our email server.
Kali Linux: A Debian-based Linux distribution tailored for penetration testing and ethical
hacking. It comes pre-installed with a wide range of tools for vulnerability assessment,
exploitation, wireless testing, and digital forensics.
VirtualBox VMs
VirtualBox will be used as our hypervisor for virtualization. Reference below for Virtual
Machine specifications.
VM Name Operating System Specs Storage
(minimum)
[project-x-dc] Windows Server 2025 2 CPU / 4096 MB 50 GBs
[project-x-win-client] Windows 11 Enterprise 2 CPU / 4096 MB 80 GBs
[project-x-linux-client] Ubuntu 22.04 Desktop 1 CPU / 2048 MB 80 GBs
[project-x-sec-work] Security Onion 1 CPU / 2048 MB 55 GBs
[project-x-sec-box] Ubuntu 22.04 Desktop 2 CPU / 4096 MB 80 GBs
[project-x-email-svr] Ubuntu Server 22.04 1 CPU / 2048 MB 25 GBs
[project-x-attacker] Kali Linux 2024.2 1 CPU / 2048 MB 55 GBs
Tools
Enterprise Tools + Defense
Microsoft Active Directory: A directory service used for managing and organizing network
resources, users, and permissions in a Windows environment.
Wazuh: An open-source security monitoring platform that provides intrusion detection, log
analysis, vulnerability detection, and compliance reporting.
Postfix: A popular open-source mail transfer agent (MTA) used for sending and receiving email
on Unix-like operating systems.
Offense
Evil-WinRM: A powerful Ruby-based Windows Remote Management (WinRM) client used by
penetration testers to connect to and interact with Windows systems, often for post-
exploitation tasks such as command execution and data extraction.
Hydra: A fast and flexible password-cracking tool designed to perform brute-force and
dictionary-based attacks on various network protocols, including SSH, HTTP, FTP, and more.
SecLists: A comprehensive collection of penetration testing resources, including wordlists for
usernames, passwords, web directories, and other payloads used in reconnaissance and
exploitation phases.
NetExec: A network exploitation tool that enables remote command execution on target
machines through various protocols, assisting in lateral movement and privilege escalation
scenarios.
XFreeRDP: An open-source implementation of the Remote Desktop Protocol (RDP), enabling
penetration testers to connect to and control Windows systems remotely for reconnaissance
and post-exploitation purposes.
Guides Numerical Order
Below is the numerical order for the step-by-step guides. These guides serve as the basis for the
project. It is recommended the respective guide is opened while following along in the program.
� If you prefer to follow content by reading, these guides will provide the same
information as the video lectures.
Guides
1. [Guide] A Primer On Provisioning Virtual Machines with VirtualBox
2. [Guide] Build a Directory Service Server With Active Directory
3. [Guide] Provision & Setup Windows 11 Enterprise
4. [Guide] Provision & Setup Ubuntu Desktop 22.04
5. [Guide] Provision & Setup Ubuntu Server 22.04
6. [Tool Guide] Setup Postfix Mail Transfer Agent
7. [Guide] Provision & Setup Security Onion
8. [Guide] Security Server - Provision & Setup Ubuntu Desktop 22.04
9. [Tool Guide] Setup Wazuh
10. [Guide] Configure a Vulnerable Environment
11. [Guide] Setup The Attacker Machine
12. [Guide] Cyber Attack - Initial Access To Breached
