Evasion Techniques and Breaching Defences (PEN-300) 90 days

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90-day access to virtual lab environment

Evasion Techniques and Breaching Defences (PEN-300) is an advanced penetration testing course. It builds on the knowledge and techniques taught inPenetration Testing with Kali Linux (PWK), teaching students to perform advanced penetration tests against mature organizations with an established security function.

As a general rule, it will not specifically deal with the act of evading a blue team but rather focus on bypassing security mechanisms that are designed to block attacks. This course is one of the replacements for the Cracking the Perimeter (CTP) course - retired October 15, 2020.

The Offensive Security Experienced Penetration Tester certification (OSEP) is an advanced penetration testing cert. We recommend starting with PWK and earning the OSCP penetration testing certification first. Once students have completed the PEN-300 course material and practiced their skills in the labs, they;re ready to take the certification exam.

The OSEP exam has a 48-hour time limit and consists of a hands-on penetration test in our isolated VPN network. Students will receive the exam and connectivity instructions for an isolated network for which they have no prior knowledge or exposure. The network will simulate a corporate network in which they must attempt to compromise targets. This exam is included and proctored.
Target Audience

Evasion Techniques and Breaching Defences is an advanced course designed for OSCP-level penetration testers who want to develop their skills against hardened systems.


We strongly suggest that students taking PEN-300 have either taken PWK and passed the OSCP certification, or have equivalent knowledge and skills in the following areas:
  • Working familiarity with Kali Linux and Linux command line
  • Solid ability in enumerating targets to identify vulnerabilities
  • Basic scripting abilities in Bash, Python, and PowerShell
  • Identifying and exploiting vulnerabilities like SQL injection, file inclusion, and local privilege escalation
  • Foundational understanding of Active Directory and knowledge of basic AD attacks
  • Familiarity with C# programming is a plus
  • Bypass defences
  • Perform advanced attacks while avoiding detection
  • Compromise systems configured with security in mind
  • Those who complete the course and pass the 48-hour exam earn the Offensive Security Experienced Penetration Tester (OSEP) certification
  • Preparation for more advanced field work
  • Knowledge of breaching network perimeter defences through client-side attacks, evading antivirus and allow-listing technologies
  • How to customise advanced attacks and chain them together

This course is the next step for penetration testers who have completed the OSCP. Topics covered include:
  • Operating System and Programming Theory
  • Client Side Code Execution With Office
  • Client Side Code Execution With Jscript
  • Process Injection and Migration
  • Introduction to Antivirus Evasion
  • Advanced Antivirus Evasion
  • Application Whitelisting
  • Bypassing Network Filters
  • inux Post-Exploitation
  • Kiosk Breakouts
  • Windows Credentials
  • Windows Lateral Movement
  • Linux Lateral Movement
  • Microsoft SQL Attacks
  • Active Directory Exploitation
  • Combining the Pieces
  • Trying Harder: The Labs
Supporting your self-paced learning
  • 19+ hours of video
  • 700-page PDF course guide
  • Active student forums
  • Access to virtual lab environment for 60 days
Exam details
  • Register at least 10 days prior to desired start date
  • Establish connection to the virtual lab
  • Progress through course materials and practice your skills
  • Schedule certification exam within 120 days of course completion
  • Successfully complete 48-hour exam and earn your OSEP


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