The OSCP exam is one of the toughest certifications in cybersecurity. It demands discipline, hands-on skills, and a deep understanding of ethical hacking. A friend of mine attempted the exam three times — and failed each one. But on the fourth attempt, he finally passed.
What changed?
Not his intelligence.
Not his luck.
His study strategy.
Below is the exact study plan that transformed his approach — and it can do the same for anyone preparing for OSCP or advancing in penetration testing.
1. Master the Fundamentals Before Touching Advanced Topics
One of his biggest mistakes was jumping into advanced tools without understanding the basics.
He corrected this by focusing on:
- Linux and Windows fundamentals
- TCP/IP, networking, and services
- File systems, permissions, privilege escalation basics
- How web apps work (forms, headers, cookies, sessions)
Why this matters:
OSCP rewards understanding and methodology — not memorizing commands.
2. Follow a Structured Daily Practice Routine
The successful plan involved a simple but powerful rule:
2–3 hours daily, no skipping days.
His weekly structure looked like this:
- Mondays: Enumeration and scanning practice
- Tuesdays: Privilege escalation labs
- Wednesdays: Web exploitation
- Thursdays: Buffer overflow practice
- Fridays: TryHackMe / Hack The Box machines
- Weekend: Review notes + do one full machine end-to-end
This consistent repetition built speed, confidence, and muscle memory.
3. Learn to Think Like an OSCP Examiner
He stopped relying on random YouTube videos and started focusing on exam-style methodology:
- Enumerate everything
- Document everything
- Always check for low-hanging fruit
- Look for misconfigurations before exploits
- Never assume a service is “not important”
- Always try multiple payloads and privilege escalation paths
This mindset shift alone increased his success rate on practice machines dramatically.
4. Build a Personal Notes Library (The “OSCP Bible”)
He created a clean, well-organized notes system containing:
- Enumeration commands
- Privilege escalation checklists
- Reverse shell one-liners
- Common misconfigurations
- Exploit modification templates
- Step-by-step methods for each attack technique
During the exam, this became his secret weapon.
OSCP rewards those who stay organized.
5. Practice Realistic Machines — Not Easy Ones
He stopped wasting time on beginner boxes and focused on medium/hard boxes similar to OSCP difficulty.
Sources he used included:
- Hack The Box (TJ Null OSCP list)
- TryHackMe (Offensive Pentesting Path)
- VulnHub (OSCP-like series)
This made the exam feel familiar instead of overwhelming.
Final Result
With the new system:
✔ His enumeration improved
✔ His privilege escalation became faster
✔ His exam workflow became clean and structured
✔ His confidence skyrocketed
On the fourth attempt, he earned his OSCP.
Want a Proven Shortcut to OSCP-Level Skills?
If you want a guided, beginner-friendly path to the skills needed for OSCP, penetration testing, Python automation, and real-world ethical hacking, my cybersecurity course is built exactly for students like you.
Inside the course, you’ll get:
✅ Hands-on hacking labs
✅ Python for cybersecurity scripts
✅ Real-world penetration testing workflows
✅ Vulnerability scanning automation
✅ Step-by-step lessons, tools, and exercises
✅ Clear explanations — no guessing
✅ A structured roadmap (unlike jumping blindly around the internet)
This is the exact kind of roadmap my friend wished he had before his first OSCP attempt.
