OSCP Enterprise Homelab

A fully documented, enterprise-inspired cybersecurity lab built on Proxmox for practicing penetration testing, Active Directory exploitation, privilege escalation, pivoting, web application attacks, and professional reporting.


Overview

This repository documents the design, deployment, and operation of a reusable cybersecurity lab that closely resembles a small enterprise network.

The primary goal is to create a repeatable environment where attacks can be practiced safely and reset to a known-good state using Proxmox snapshots.

Unlike many "vulnerable VM" collections, this lab emphasizes realistic infrastructure and attack paths. Machines exist for a reason, users belong to departments, and services are deployed similarly to what an internal penetration tester would encounter.


Objectives

  • Learn enterprise networking
  • Build an Active Directory environment
  • Practice OSCP-style methodology
  • Learn Windows and Linux privilege escalation
  • Practice web application testing
  • Practice buffer overflow exploitation
  • Learn lateral movement and pivoting
  • Build professional documentation habits
  • Maintain a reusable cyber range

Lab Architecture

                     Internet
                         |
                    Home Router
                         |
                      Proxmox
                         |
                    vmbr0 (WAN)
                         |
                      pfSense
             +-----------+-----------+
             |                       |
      vmbr1 (Attack)          vmbr2 (Corporate)
             |                       |
          Kali Linux           Active Directory
                               Windows Clients
                               SQL Server
                               File Server
                               Linux Targets
                               Buffer Overflow VM

                     vmbr3 (DMZ)
                         |
                 Public Web Targets

Repository Layout

homelab/
├── README.md
├── diagrams/
├── docs/
├── playbooks/
└── assets/

Documentation

File Purpose
01-proxmox.md Proxmox installation and virtualization
02-pfsense.md Firewall and routing
03-networking.md Network design and IP addressing
04-active-directory.md Domain deployment
05-kali.md Attacker workstation
06-vulnerable-machines.md Windows/Linux targets
07-pivoting.md Internal routing and tunneling
08-buffer-overflow.md Dedicated BOF machine
09-web-attacks.md Web application testing
10-privilege-escalation.md Windows/Linux PrivEsc
11-attack-methodology.md Full penetration testing workflow
12-resetting-the-lab.md Snapshots and restoration
troubleshooting.md Common issues

IP Addressing

Network Purpose
192.168.1.0/24 Home LAN
10.10.10.0/24 Attacker Network
10.10.20.0/24 Internal Corporate LAN
10.10.30.0/24 DMZ

Virtual Machines

Machine Purpose
pfSense Firewall and routing
Kali Linux Attacker workstation
DC01 Active Directory
WIN10-01 Domain workstation
WIN10-02 Domain workstation
FILE01 SMB enumeration
SQL01 MSSQL attacks
WEB01 Web exploitation
LINUX01 Linux privilege escalation
BOF-WIN7 Buffer overflow practice
PIVOT01 Pivoting and tunneling

Learning Workflow

Each exercise should follow the same methodology:

  1. Reconnaissance
  2. Enumeration
  3. Vulnerability Identification
  4. Initial Access
  5. Privilege Escalation
  6. Credential Harvesting
  7. Pivoting
  8. Lateral Movement
  9. Domain Compromise
  10. Documentation
  11. Restore Snapshot

Snapshot Philosophy

Every virtual machine should maintain at least one baseline snapshot.

Recommended naming convention:

BASE_INSTALL
DOMAIN_JOINED
VULNERABLE
READY_FOR_ATTACK

Rollback should always return the machine to a known state within seconds.


Documentation Standards

Every completed attack should include:

  • Objective
  • Enumeration
  • Exploitation
  • Privilege Escalation
  • Screenshots
  • Commands Used
  • Lessons Learned
  • Detection Opportunities
  • Mitigations

Long-Term Goals

Future improvements include:

  • SIEM integration
  • Wazuh
  • Sysmon
  • BloodHound
  • Elastic Stack
  • Terraform
  • Ansible
  • Automated lab deployment
  • Continuous lab documentation through Wiki.js
Description
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Readme 42 KiB