⏎Avoiding Common OSCP Pitfalls🕳

Robert Scocca
17 min readMay 19, 2021

Learn from painfully common mistakes that contributed to my initial failure and how to pass the Offensive Security Certified Professional exam. I went from a 35 point fail to a 100 point pass a few months later.

This post is written to help those on their ‘OSCP journey’, practicing hard on vulnerable machine platforms for their OSCP exam attempt. I want to improve your chances of passing by sharing my common mistakes, tips for successes, and how to practice most effectively. I’ve read hundreds of “OSCP journey” or “OSCP review” type posts like this one during my dive into the OSCP. I’m well aware of the common mistakes from first and second hand experience. This post is my accumulation all of that experience.

What you will learn from this post:

  • How not to fall into common OSCP learning pitfalls
  • Best ethical hacking platform to practice for OSCP exam
  • Essentials tools to use every day during OSCP prep
  • Insights on lab report and hacking methodology

Initial Prep

The summer of 2020 I began my OSCP studies. I had minimal experience with hacking vulnerable machines. I’ve played around with Hack the Box and VulnHub a little bit, but that’s all. I purchased 2 month of PWK lab access. A whole month of that time was spent reading the PWK text book and completing all the exercises. My lab report turned out to be nearly 500 pages which was definitely not worth it(more on that later)…

The second month was spent in the PWK lab environment. Then I spent one more month doing TJnulls OSCP-like Hack the Box list, including doing some of the VulnHub boxes listed on there. I also completed Tib3rius Windows and Linux Privilege Escalation Udemy courses and The Cyber Mentor’s Pratical Ethical Hacking Udemy course. Ofcourse I took a great abundance of notes on the courses I took and the vulnerable machines hacked.

How to Fail

I found out quickly on exam day that I bit off more than I chew.

I cracked the buffer over flow and the 10 point machine the first couple of hours, then got stumped for the rest of the exam. I was able to find remote code execution on one machine but couldn’t get a shell on the target even after trying different shell spawning commands for hours.

Hints and Write-ups