An In-Depth Look at PEN-300 and OSEP: Succeeding in the Offensive Security Path

In the dynamic landscape of penetration testing, knowledge growth is a perpetual journey. Leading this learning curve is the Offensive Security Experienced Penetration Tester (OSEP) certification, offered through the PEN-300 course by Offensive Security. This credential is a renowned benchmark for advanced penetration testers and red teamers around the globe. This article shares my personal experience with the course, discussing the interesting hurdles I encountered and the joy of passing the final exam successfully.

The Genesis: Setting the Groundwork

Embracing the PEN-300 course requires an individual to immerse themselves in a world of complex cyber threat landscapes and advanced penetration techniques. Spread over 90 days, this course required me to dedicate between 24 to 32 hours per week, a commitment that was divided between video lectures, reading course materials, and performing lab exercises. The provided course materials, which included in-depth PDF and video lectures, played a pivotal role in setting a steady pace and structure for my learning journey.

Curriculum Design: A Structured Approach to Learning

The design of the PEN-300 course is ingenious. The course is cleverly designed, beginning with simple topics and gradually becoming more complex to mimic the tricky situations you might face in actual penetration testing. One of the standout features of the course design is the “Extra Miles” challenges. These are exercises designed to push you outside your comfort zone, compelling you to think beyond the conventional frameworks and explore creative problem-solving methods.

Lab Exercises: Practical Application of Theoretical Knowledge

The PEN-300 course heavily emphasizes hands-on lab exercises. These labs offered a platform to apply the theoretical concepts and techniques learned from the lectures in a controlled, safe environment. Each lab, including the ‘Extra Miles’ exercises, was designed to present unique learning scenarios that required multiple attempts and a lot of revisits, ensuring a thorough understanding and mastery of the concepts.

Mastering AMSI Bypass and AV evasion Techniques and Tactics

A significant portion of the PEN-300 course was dedicated to mastering the Anti-Malware Scan Interface (AMSI) bypass techniques and AV evasion tactics. The process of understanding, developing, and executing AMSI bypasses formed an integral part of the curriculum, providing me with an essential skill set that would prove invaluable when faced with high-security systems in real-world scenarios. This segment was both a challenging and enlightening experience.

The Ultimate Challenge: The Exam

The PEN-300 course culminated in a challenging exam that required capturing flags in a simulated network. The exam spanned over two days (48 hours) and tested not only the knowledge I had acquired over the course but also my endurance, determination, and problem-solving abilities.

For the exam, I utilised the custom tools I had developed during the labs. The need to adapt these tools to various scenarios underscored the importance of understanding their functionalities and potential limitations. These custom tools were not just a learning experience, but an essential part of automating processes and moving faster in the exam. They allowed me to create custom payloads, shells, evasions, and more.

Creating Custom Tools: Stepping Up the Game

The PEN-300 course strongly emphasises creating custom tools to exploit system vulnerabilities. This aspect of the course allowed me to create Fully Undetected (FUD) payloads, which are capable of bypassing standard defense mechanisms. Developing these tools not only added a powerful weapon to my arsenal but also provided valuable practical experience, preparing me for real-world, high-stakes scenarios.

Some of these custom tools that I developed can be found on my GitHub account at GitHub.com/xbz0n.

Enhancing Skills: Bridging the Gap Between Theory and Practice

The PEN-300 course has significantly boosted my skills in many areas. Beyond learning the nuts and bolts of advanced exploitation, the course also taught me the importance of persevering, thinking creatively, and navigating through challenges. This journey enhanced my technical knowledge, and problem-solving skills, and honed my ability to persevere in the face of adversity.

Final Thoughts: The Payoff

This journey has enriched my professional portfolio and equipped me with the skills, knowledge, and confidence to face complex penetration testing scenarios.

Obtaining the OSEP was a demanding yet rewarding endeavor. True to Offensive Security’s mantra, ‘Try Harder,’ the course demanded perseverance, dedication, and an insatiable curiosity about penetration testing. My journey to OSEP is a testament to the robustness of the course and the valuable skills it imparts. These skills and experiences are invaluable to any penetration tester or red teamer looking to expand their capabilities and delve into the fascinating world of advanced exploitation techniques.

The journey was challenging but exciting, and the triumphant success in the exam was a satisfying culmination of this journey. The real-world skills I gained will be instrumental in my professional journey, and I am confident in taking on even more significant challenges.