Penetration Testing Advanced

Advanced Penetration Testing

Marcus Rodriguez
12 weeks

Course Overview

Course Overview

Advanced Penetration Testing is designed for security professionals who want to take their ethical hacking skills to the next level. This intensive 12-week course covers sophisticated attack techniques used in real-world penetration tests.

What Makes This Course Advanced

  • Real-World Scenarios: Work with enterprise-level environments
  • Custom Exploit Development: Learn to write your own exploits
  • Professional Methodology: Follow industry-standard penetration testing frameworks
  • Comprehensive Coverage: From reconnaissance to reporting
  • Hands-On Focus: 80% practical labs, 20% theory

Course Objectives

By completing this course, you will be able to:

  1. Conduct comprehensive penetration tests of complex environments
  2. Develop custom exploits for specific vulnerabilities
  3. Compromise and pivot through enterprise networks
  4. Attack Active Directory environments
  5. Write professional penetration testing reports
  6. Prepare for OSCP, GPEN, or similar certifications

Target Audience

This course is ideal for:

  • Security professionals with basic penetration testing experience
  • Systems administrators wanting to understand attacker techniques
  • Security consultants looking to expand their skillset
  • Bug bounty hunters seeking advanced techniques
  • Anyone preparing for OSCP or GPEN certification

Lab Environment

You’ll work with:

  • Kali Linux: Primary attacking machine
  • Vulnerable Networks: Custom lab environments with multiple machines
  • Active Directory Lab: Simulated enterprise environment
  • Web Application Lab: Complex, multi-tier applications
  • Cloud Environments: AWS/Azure security testing

All labs are isolated and can be accessed remotely.

Assessment & Certification

  • Weekly Labs: 40% of final grade
  • Midterm Practical Exam: 20% of final grade
  • Final Capstone Project: 30% of final grade
  • Report Writing Assignments: 10% of final grade

Required Tools

  • Kali Linux (Virtual Machine)
  • Burp Suite Professional (trial license provided)
  • Metasploit Framework
  • BloodHound
  • Custom scripts provided in course repository

Detailed Syllabus

Module 1: Advanced Reconnaissance (Weeks 1-2)

Theory: Information gathering methodologies, OSINT frameworks, passive vs. active reconnaissance

Practical Labs:

  • OSINT investigation of a target organization
  • DNS enumeration and subdomain discovery
  • Network mapping of complex environments
  • Social engineering information gathering exercise

Module 2: Exploitation Techniques (Weeks 3-4)

Theory: Exploit development fundamentals, understanding memory corruption, shellcode development

Practical Labs:

  • Writing a buffer overflow exploit
  • Developing custom Metasploit modules
  • Bypassing ASLR and DEP
  • Exploiting known CVEs in the lab environment

Module 3: Post-Exploitation (Weeks 5-6)

Theory: Post-exploitation frameworks, privilege escalation methodology, persistence techniques

Practical Labs:

  • Windows privilege escalation
  • Linux privilege escalation
  • Establishing persistence mechanisms
  • Data exfiltration and covert channels
  • Lateral movement through networks

Module 4: Active Directory Attacks (Weeks 7-8)

Theory: Active Directory architecture, Kerberos authentication, AD attack paths

Practical Labs:

  • Kerberoasting attacks
  • Golden and Silver Ticket creation
  • Pass-the-Hash attacks
  • BloodHound AD enumeration
  • Achieving domain admin access

Module 5: Advanced Web Testing (Weeks 9-10)

Theory: Modern web application architecture, advanced vulnerability classes

Practical Labs:

  • SSRF exploitation
  • XXE attacks and exploitation
  • Insecure deserialization
  • Advanced XXS techniques
  • API security testing

Module 6: Capstone Project (Weeks 11-12)

Final Project: Complete penetration test of a simulated enterprise environment

You’ll conduct a full penetration test including:

  • External reconnaissance
  • External network penetration
  • Internal network exploitation
  • Active Directory compromise
  • Web application testing
  • Professional report delivery

Course Materials

Required Reading

  • “The Hacker Playbook 3” by Peter Kim
  • “Penetration Testing” by Georgia Weidman
  • PTES Technical Guidelines
  • OWASP Testing Guide v4

Video Content

  • 50+ hours of video lectures and demonstrations
  • Live recorded sessions
  • Guest lectures from industry professionals

Hands-On Labs

  • 100+ practical exercises
  • Capture-the-Flag (CTF) challenges
  • Timed exam simulations

Instructor Office Hours

  • Live Sessions: Every Tuesday and Thursday, 7-9 PM EST
  • On-Demand Support: GitHub Discussions
  • Emergency Support: For lab access issues

Community

Join our vibrant learning community:

  • Discord Server: Real-time chat and collaboration
  • GitHub Repository: Share scripts and tools
  • Weekly Meetups: Virtual study groups
  • Mentorship Program: Connect with experienced pentesters

Career Outcomes

Graduates of this course have gone on to:

  • Pass OSCP, GPEN, GXPN certifications
  • Land penetration testing roles at major firms
  • Start successful bug bounty careers
  • Launch security consulting businesses

Prerequisites Review

Before enrolling, ensure you have:

✅ Strong Linux command-line skills ✅ Understanding of TCP/IP networking ✅ Basic scripting knowledge (Python, Bash) ✅ Familiarity with web technologies ✅ Security+ level knowledge or equivalent ✅ 40+ hours per week for coursework

Getting Started

  1. Enroll: Submit your enrollment request
  2. Access Check: Verify you meet prerequisites
  3. Setup: Configure your lab environment (Week 0)
  4. Orientation: Attend the live orientation session
  5. Begin: Start Week 1 reconnaissance module

This is an intensive, demanding course that will push your skills to new heights. If you’re ready to become an advanced penetration tester, enroll now!

Note: This course focuses on ethical hacking for defensive purposes. All techniques must be used legally and ethically.

Detailed Syllabus

01

Advanced Reconnaissance

Deep information gathering and OSINT techniques

  • OSINT Framework and Tools
  • DNS Enumeration and Subdomain Discovery
  • Network Mapping and Service Identification
  • Social Engineering Information Gathering
02

Exploitation Methodologies

Advanced exploitation techniques and custom exploit development

  • Buffer Overflow Exploitation
  • Return-Oriented Programming (ROP)
  • Exploit Development Fundamentals
  • Metasploit Framework Mastery
03

Post-Exploitation

Maintaining access and expanding compromise

  • Privilege Escalation Techniques
  • Persistence Mechanisms
  • Data Exfiltration Methods
  • Covering Tracks and Anti-Forensics
04

Active Directory Attacks

Attacking Windows environments and AD

  • Kerberos Attacks (Golden/Silver Tickets)
  • Pass-the-Hash and Pass-the-Ticket
  • BloodHound and AD Enumeration
  • Domain Dominance Techniques
05

Advanced Web Application Testing

Complex web application vulnerabilities

  • Server-Side Request Forgery (SSRF)
  • XML External Entity (XXE) Attacks
  • Insecure Deserialization
  • Business Logic Vulnerabilities
06

Professional Reporting

Creating comprehensive penetration testing reports

  • Report Structure and Components
  • Effective Vulnerability Documentation
  • Executive Summary Writing
  • Remediation Recommendations