🔴 Advanced Penetration Testing & Pivoting Lab

Author: Md. Jipel Ahamed Arman
Cybersecurity Enthusiast | Penetration Testing | Red Teaming | Network Security

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📖 Project Overview

This project documents the design and execution of a professional cybersecurity home lab built using VMware Workstation. The environment simulates a realistic, segmented enterprise network, specifically designed to practice the transition from initial access to internal network compromise.

Core Focus Areas:

• Vulnerability Assessment & Exploitation
• Privilege Escalation (Linux/Windows)
• Internal Network Enumeration & Pivoting
• Lateral Movement & Post-Exploitation

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🧠 Lab Architecture

The environment is logically segmented into two distinct zones to simulate a perimeter-based defense.

Zone 1: External Network (192.168.50.0/24)

• Kali Linux: Primary Offensive Platform.
• Metasploitable 2 (The Pivot): A dual-homed vulnerable web server acting as the bridge.
  • eth0: Connected to External Network.
  • eth1: Connected to Internal Network.

Zone 2: Internal Network (10.10.10.0/24)

• Domain Controller: Windows Active Directory Services.
• App Server: Internal Corporate Application Host.
• Employee Workstation: Windows 10 Client System.

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⚔️ Activities Performed

1. Reconnaissance & Enumeration

• Host Discovery: netdiscover, ARP scanning.
• Service Mapping: Full Nmap TCP/UDP port scans and banner grabbing.
• Vulnerability Research: Mapping services to known CVEs using Searchsploit.

2. Exploitation

Successfully gained initial access through multiple vectors:

• vsftpd 2.3.4 Backdoor (CVE-2011-2523)
• Samba usermap_script (CVE-2007-2447)
• PHP CGI Argument Injection (CVE-2012-1823)
• Credential Attacks: SSH/Telnet brute-forcing and MySQL default credential exploitation.

3. Pivoting & Lateral Movement

• Proxychains & SSH Tunneling: Routing traffic through the compromised Metasploitable host to reach the 10.10.10.0/24 segment.
• Meterpreter Routing: Utilizing MSF post-exploitation modules to automate internal routing.

4. Privilege Escalation & Post-Exploitation

• Local Escalation: Exploiting misconfigurations to gain ROOT and SYSTEM privileges.
• Credential Harvesting: LSASS memory dumping, NTLM hash extraction, and Token Impersonation.

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🧰 Tools & Technologies

• Hypervisor: VMware Workstation Pro
• OS: Kali Linux, Metasploitable 2, Windows Server, Windows 10
• Frameworks: Metasploit, Proxychains
• Scanning: Nmap, Netdiscover
• Cracking: Hashcat, John the Ripper

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📄 Included Reports

This repository includes detailed documentation of the lab's lifecycle:

1. [Isolated VMware Lab Setup]
2. [Vulnerability Assessment Metasploitable 2]
3. [Full Penetration Testing Execution Report]

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⚠️ Disclaimer

This project was conducted in a fully isolated and authorized lab environment for educational purposes only. Unauthorized access to computer systems is illegal. Always follow ethical guidelines and the rules of engagement.