Passing the Offensive Security Experienced Penetration Tester (OSEP) exam on July 1st was a feat that truly tested my resolve and dedication. After a rigorous six-month preparation period, where I immersed myself in the Learn One course offered by OffSec, I approached my first attempt with confidence. However, the reality check was harsh; I managed to secure only 2 flags. The initial setback was disheartening, but it didn’t deter me. I buckled down for another 2–3 months, revisiting the comprehensive course material, delving deeper into the labs, and completing all the ‘extra mile’ challenges.
My preparation was not that intense initially. I dedicated roughly 10–15 hours each week, totaling nearly a year of consistent study. Despite this, my second attempt was a near-miss. With the Learn One program at its end, I captured 8 flags but ran a grueling marathon with minimal sleep — just 10 hours over the 48-hour exam duration — and took multiple short breaks to maintain focus. The pressure to succeed was immense; I couldn’t just walk away after investing so much time and effort.
Undeterred, I purchased another exam voucher. With a renewed sense of purpose, I meticulously reviewed all the materials, compiled code locally, and ensured I understood the exam’s themes intimately. By my third attempt, I was not just a candidate but a seasoned warrior familiar with the battleground. This time the exam felt different; the challenges seemed to flow, and within the first 24 hours, I had captured 8 flags.
However, complacency wasn’t an option — the 9th flag eluded me for a full 8 hours. But once overcome, the remaining challenges fell into place, and I secured 12 flags in total. With 8 hours to spare, I turned my attention to the critical task of reporting — a component of the OSEP that should never be underestimated. I painstakingly verified each screenshot and documented every required step, keenly aware that any oversight could cost me my success on this third and crucial attempt.
The importance of clear, concise reporting cannot be overstated. It is vital to capture every detail, narrate the attack steps accurately, and articulate the findings in good, understandable English. For those preparing for the OSEP, I recommend studying existing reviews online. They offer a treasure trove of insights but don’t just read them — analyze and build upon them to create a personalized study plan that suits your learning style and schedule.
The OSEP journey is as challenging as it is rewarding, and persistence is key. To those on the path to this certification, remember that each attempt is a learning experience paving the way to your ultimate goal. Keep pushing forward, and success will be yours.
PEN-300 Advice
- Depth of Course Material: The PEN-300 course is known for its in-depth and advanced content, focusing on high-level penetration testing techniques. It goes beyond the basics and challenges students with real-world scenarios. Make sure to complete both text and videos. This would also give you the opportunity to learn or understand the basics of C# and you might ending up creating new projects for your GitHub repository.
- Lab Environment: The hands-on lab environment is a critical component of the learning experience. It is designed to simulate a realistic network in which students can practice and refine their penetration testing skills. Complete all the labs and you’ll understand at the end that how important is to complete those labs not just for the exam but also for the real world environment testing.
- Extra Miles: The course includes “Extra Miles” challenges that encourage students to go beyond the standard lab exercises. Completing these provides a deeper understanding of the material and provides you many different ways to evade the not only Windows Defender but you can evade different EDR as well.
- Courses: In terms of Active Directory, I strongly advise you to do CRTP and CRTO before OSEP. Both covers AD extensively and different techniques, to complete the labs. These courses will provides excellent value as well!
- Reporting: One of the most emphasized aspects of the course is the importance of reporting. Not only do students need to successfully exploit systems, but they also need to document their findings clearly and professionally. So take good notes and as many screenshots as you can while compromising the machines. Take and write down all the steps before you move to the next part and make sure to find all the flags in a compromised machines.
- Time Management: The course and subsequent exam test one’s ability to manage time effectively. Successful students often create a schedule or strategy to ensure they cover all necessary topics and lab exercises before attempting the exam.
- Community Support: Leveraging the community, such as forums and study groups, is often mentioned as an invaluable resource. Engaging with peers can provide insights and help clarify difficult concepts. The Off Sec community is fantastic, and they have a Discord server as well as a Student Forum. The Discord community is strong, and Off Sec staff can help you if you run across any issues throughout the challenges or labs.
- Persistence and Resilience: The challenging nature of both the labs and the exam demands an attitude that not only accepts difficulties but also sees them as valuable learning opportunities. It’s about cultivating resilience, the kind that propels you forward through obstacles and transforms setbacks into stepping stones for success. So keep grinding the material and labs. You’ll learn a lot and feel like a different person (penetration tester) after you complete all the material and passed the exam.
Conclusion
In PEN-300 material, you’ll find that some parts may not be the most exciting, while others can be quite engaging — I think that’s just part of the journey with any certification you pursue. Nonetheless, this has been my top pick among all the Off Sec certifications I’ve tackled, and I would wholeheartedly recommend it to anyone considering it!
Backdoor
