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How I Passed the OSCP with 110 Points

August 5, 2023
by Kieran Jessup
oscpcertificationpenetration-testingoffensive-securitycareer

Quick Answer

I passed the OSCP (Offensive Security Certified Professional) exam with 110 points in July 2023 after 7 months of dedicated study. The key to my success was a structured approach combining official PWK labs, Proving Grounds practice, and consistent hands-on experience with 38 Proving Grounds labs and 20 HackTheBox machines.

My OSCP Journey Timeline

January 2023: Foundation Building

  • LearnOne Activated: Started my official OSCP journey with OffSec’s LearnOne subscription

February 2023: PWK Exercise Phase

  • Started PWK Exercises: Began working through the official Penetration Testing with Kali Linux exercises
  • Methodology Development: Focused on building systematic enumeration and exploitation approaches
  • Documentation Practice: Started developing comprehensive note-taking and reporting skills, started with Obsidian but moved to Notion.

March 2023: Lab Completion & Transition

  • Completed 2022 PWK Exercises: Finished all exercises from the previous year’s courseware
  • PWK 2023 Release: Transitioned to the updated course material with new content
  • Active Directory Focus: Completed the AD portion of the 2023 PWK labs
  • Bonus Points Achieved: Secured additional points through lab completion

April 2023: Life Events & Competition

  • Got Married: Took time for personal milestone while maintaining study momentum
  • ADF Hackathon: Competed in the Australian Defence Force hackathon for practical experience
  • Balanced Approach: Learned to maintain study consistency during major life events

May 2023: Advanced Practice

  • OffSec Proving Grounds: Intensified practice with Proving Grounds labs
  • OSCP Labs: Completed MedTech and Relia labs for additional experience
  • Skill Refinement: Focused on improving speed and accuracy in exploitation

June 2023: Final Preparation

  • HTB Pro Lab: Dante: Completed the advanced HackTheBox Dante lab
  • Mock Exams: Successfully completed OSCP Mock exams A, B, and C
  • Exam Readiness: Built confidence through consistent mock exam success

July 2023: Certification Achieved

  • OSCP Exam: Sat and passed the 24-hour practical exam
  • 110 Points: Achieved a strong score demonstrating comprehensive understanding
  • OSCP Certified: Officially became an Offensive Security Certified Professional

Study Resources That Worked

Primary Learning Platforms

Official OffSec Materials

  • PWK Courseware (2022 & 2023 versions) - Essential for understanding OffSec’s methodology
  • OSCP Labs (MedTech, Relia) - Direct preparation for exam environment
  • Proving Grounds Practice Labs - Additional practice with realistic scenarios
  • Official Discord Community - Support and knowledge sharing

Third-Party Resources

  • TCM Security Courses - Alternative explanations and methodologies
  • TJ NULL Trophy Room - Curated vulnerable machines
  • Hack The Box Academy - Structured learning modules
  • YouTube Channels (OverGrownCarrot1, IPPSEC) - Visual learning and walkthroughs

Practice Platforms

  • OffSec Proving Grounds - Additional practice with realistic scenarios
  • HackTheBox Machines - Exposure to diverse vulnerability types
  • HTB Pro Labs (Dante) - Advanced enterprise scenarios
  • Mock Exams (A, B, C) - Exam environment simulation

Key Learning Resources Breakdown

1. TCM Security

  • What: Comprehensive cybersecurity training platform
  • Why It Worked: Provided alternative methodologies and explanations
  • Best For: Understanding different approaches to common techniques

2. TJ NULL Trophy Room

  • What: Curated collection of vulnerable machines
  • Why It Worked: Focused practice on specific vulnerability types
  • Best For: Targeted skill development and technique refinement

3. Hack The Box Academy

  • What: Structured learning platform with modules
  • Why It Worked: Provides solid knowledge of AD.
  • Best For: Building foundational knowledge and methodology

4. YouTube Channels

  • OverGrownCarrot1: Practical walkthroughs and real-world scenarios
  • IPPSEC: Detailed technical explanations and methodology breakdowns
  • Why They Worked: Visual learning and different perspectives on techniques

What Worked for Me: Proven Strategies

1. Active OffSec Discord Participation

Why It Was Critical:

  • Community Support: Access to experienced professionals and fellow students
  • Knowledge Sharing: Learned from others’ approaches and methodologies whilst sharing my own knowledge. I found it helpful as teaching others reinforced my own concepts plus if I was wrong I would be called out by more experienced members. It was a form of QA really.
  • Motivation: Stayed engaged through community interaction
  • Problem Solving: Got help when stuck on difficult concepts

How to Maximize Discord Benefits:

  • Ask Questions: Don’t hesitate to seek clarification
  • Share Solutions: Contribute to the community knowledge base
  • Follow Channels: Stay updated on course changes and announcements
  • Network: Build relationships with other security professionals

2. Proving Grounds Labs

Why They Were Essential:

  • Realistic Scenarios: Closest to actual exam environment
  • Variety: Different difficulty levels and vulnerability types
  • Practice: Consistent hands-on experience
  • Confidence Building: Success in labs translated to exam confidence

Proving Grounds Strategy:

  • Start Easy: Begin with easier machines to build confidence
  • Gradual Progression: Move to more difficult machines as skills improve
  • Time Management: Practice completing machines within time constraints
  • Documentation: Maintain detailed notes for each machine

3. Structured Study Approach

Timeline Management:

  • Consistent Schedule: Dedicated study time each day/week
  • Milestone Tracking: Set specific goals for each month
  • Adaptation: Adjusted study plan based on progress and life events
  • Balance: Maintained study momentum during personal commitments

My OSCP Statistics

Lab Completion Summary

OSCP Labs (100% Completion)

  • MedTech Lab: Completed successfully
  • Relia Lab: Completed successfully
  • PWK Exercises: All exercises from both 2022 and 2023 versions
  • Bonus Points: Achieved through lab completion

Proving Grounds (38 Labs)

  • Difficulty Range: Easy to difficult machines
  • Vulnerability Types: Web applications, privilege escalation, Active Directory
  • Methodology Practice: Systematic enumeration and exploitation approaches
  • Time Management: Practice completing machines within exam timeframes

HackTheBox (20 Machines)

  • Platform Variety: Different operating systems and scenarios
  • Skill Development: Targeted practice on specific techniques
  • Real-World Scenarios: Exposure to realistic attack vectors
  • Community Learning: Leveraged HTB community resources

HTB Academy Module

  • Attacking Enterprise Networks: Comprehensive enterprise security module
  • Active Directory: Deep dive into AD attack techniques
  • Methodology: Structured approach to enterprise penetration testing
  • Practical Application: Real-world enterprise scenarios

Exam Day Strategy

24-Hour Exam Approach

Time Management:

  • First 4 Hours: Initial enumeration and low-hanging fruit, I went straight for the AD box but got stuck so pivoted to standalones. It turned out that my AD box needed a reboot as I got stuck again later in the day but after a reboot I quickly found my first foothold.
  • After the standalone pivot, I had all 3 standalones done within 3 hours and returned to the AD set. I was stuck here for a long time and it was almost 6 hours until I realised the box was cooked. Rebooted it and had domain admin within 3 hours.

Documentation Strategy:

  • Real-Time Notes: Document everything as you go
  • Screenshots: Capture all important findings
  • Command History: Save all commands and outputs
  • Methodology: Document your systematic approach

Career Benefits

  1. Professional Recognition: Immediate credibility in the security community
  2. Career Opportunities: Access to advanced penetration testing roles
  3. Skill Validation: Demonstrated practical security expertise
  4. Network Expansion: Connected with other OSCP holders

Skill Development

  1. Methodology: Developed systematic penetration testing approaches
  2. Tool Proficiency: Mastered essential security tools
  3. Documentation: Enhanced technical writing and reporting skills
  4. Problem Solving: Improved analytical and troubleshooting abilities

Advice for Future OSCP Candidates

Essential Tips

  1. Start with Fundamentals: Ensure strong networking and Linux knowledge
  2. Practice Consistently: Daily hands-on practice is crucial
  3. Join Communities: Engage with OffSec Discord and other communities
  4. Document Everything: Develop comprehensive note-taking habits
  5. Mock Exams: Use mock exams to build confidence and identify gaps

Common Pitfalls to Avoid

  1. Tool Dependency: Don’t rely too heavily on automated tools
  2. Poor Documentation: Inadequate notes will hurt your exam performance
  3. Time Management: Don’t spend too long on single machines
  4. Isolation: Don’t study alone - engage with the community

Conclusion

Passing the OSCP with 110 points was the result of 7 months of dedicated study, consistent practice, and almost total burnout. Make sure you’re not riding too close to the sun as it’s very common to burnout studying for this exam, in hindsight I think I massively overprepared.

Key Takeaways:

  • Structured approach with clear milestones is essential
  • Hands-on practice should be prioritized over theory
  • Community engagement provides motivation and support
  • Mock exam practice builds confidence and identifies gaps
  • Documentation skills are as important as technical skills

If you’re preparing for the OSCP, you might also be interested in these related posts:

Certification Journey:

Learning Path:

  1. Foundation: Cybersecurity Basics - Understand core concepts
  2. Practice: HTB - BountyHunter - Hands-on web security
  3. Advanced: This OSCP Journey - Certification preparation
  4. Expert: Apply OSCP skills to real-world penetration testing

External OSCP Resources:

For additional OSCP preparation, consider these resources: