Passing the OSCP (Offensive Security Certified Professional) on my first try wasn’t luck. It was the result of intense discipline, methodical preparation, and a lot of evenings staring at a terminal screen. If you’re thinking about diving into the OSCP challenge, know this: it’s tough, time-consuming, and at times overwhelming, but incredibly rewarding.
In this first part, I’ll walk through how I laid the foundation before even touching the official PEN-200 course materials. This pre-game phase made a world of difference when I finally entered the exam room.
Understanding What You’re Signing Up For
The OSCP isn’t just a test, it’s a journey. When you sign up, you’re getting access to the PEN-200: Penetration Testing with Kali Linux course, along with a virtual lab environment and one or more exam attempts, depending on your package. You can choose between 90 and 365 days of lab access, with prices ranging from $1599 to $5499. That’s a serious investment, so planning how and when to take the course matters a lot.
Even though OffSec calls it “self-paced,” the countdown starts the day you get access. If you’re unprepared, those days vanish quickly without meaningful progress. That’s why I didn’t dive in headfirst. I spent time beforehand building up the skills I’d need.
Know the Prerequisites and Actually Learn Them
The OSCP assumes you’re not a total beginner. If you’re unfamiliar with basic networking or Linux environments, you’ll struggle. OffSec outlines prerequisites: a solid grasp of TCP/IP, familiarity with Windows and Linux systems, and basic Bash or Python scripting skills. These aren’t just suggestions, they’re survival tools.
So before I purchased the course, I honestly assessed myself. I had a background in IT, years of Windows Server admin experience, and certifications like A+ and Network+, so networking wasn’t new to me. But Linux and scripting? That was another story.
Brushing Up on Networking
Even if you’ve done networking before, it’s worth brushing up. I refreshed concepts like subnetting, TCP handshakes, port scanning, ICMP protocols, DNS, and how firewalls handle traffic. You’ll need to understand these inside out when trying to figure out why a target isn’t responding or why your exploit didn’t work.
I used a few tools to help sharpen this edge. One solid resource was Exam-Labs. Their Cisco CyberOps Associate (200-201 CBROPS) course includes networking fundamentals presented in a practical and digestible way. It included videos, practice tests, and scenario-based questions – super useful when you’re thinking like an attacker, not just a sysadmin.
Learning Linux from Scratch
I won’t lie, I was a Linux noob. I could bumble my way through commands, but for OSCP, that’s not enough. You need to navigate the terminal like a second home, recognize file permissions, understand cron jobs, process management, and how services start or fail silently.
That’s where Linux Journey came in. This free online tool saved me. It breaks Linux concepts into beginner-friendly modules with small, focused lessons. I didn’t rush it. I spent weeks going through permissions, file systems, redirection, and process management.
Then, I leveled up with Bandit, one of the wargames on OverTheWire. These are real, terminal-based challenges where you SSH into a machine and solve puzzles. Some require decoding files, finding hidden scripts, or escaping restricted environments – perfect practice for what the OSCP labs will throw at you later.
Bash and Python Scripting: Understanding the Logic
Next up was scripting. You don’t need to be a software engineer, but understanding Bash and Python is crucial. You’ll use Bash for automation and quick local enumeration, and Python to analyze and modify exploits.
I started by revisiting basic Bash syntax and learning how to write simple enumeration scripts. I practiced reading and modifying sample Python scripts online, especially ones that dealt with networking, like creating simple socket servers or manipulating HTTP requests. Understanding things like loops, conditions, functions, and basic file I/O in Python is enough.
There are a ton of intro Python sites out there, but the ones I found most useful were the ones that showed real-world use cases, like sending packets or interacting with system processes. I recommend looking for Python tutorials that dive into networking and system interaction, anything that prepares you to understand tools like socket, os, and subprocess.
Virtual Hacking Labs Before the Real Deal
Once I felt semi-confident in Linux, networking, and scripting, I dipped my toes into actual hacking. I subscribed to Virtual Hacking Labs for $249. It gave me three months of access to a virtual environment with machines to exploit and a beginner-friendly course PDF.
These labs mimic the OSCP vibe, no hand-holding, no hints. You’re thrown into a network and left to your devices. It’s overwhelming at first, but it teaches you core enumeration and exploitation strategies. Tools like Nmap, Nikto, Dirb, and Netcat became my best friends.
This environment is perfect for learning how to scan, enumerate, and chain exploits. It taught me the importance of patience and note-taking, both of which become critical when you’re inside OffSec’s lab network.
Scheduling Your Course Start Date
Something I didn’t realize at the beginning: OffSec doesn’t start your course immediately after payment. You’ll pick a start date based on availability. For me, the next open slot was three weeks out. That worked out perfectly since I had a few more things I wanted to wrap up in Virtual Hacking Labs.
When you’re ready to start the course, I recommend booking a three-month block with minimal distractions. You’ll need at least two to four hours daily to stay on track. I averaged four hours a day, sometimes split between mornings and work breaks. I avoided studying after dinner to protect time with family and prevent burnout.
This is a big point: protect your energy. You don’t have to go full hermit, but treat the OSCP like a part-time job. If you show up consistently and with focus, you’ll be in great shape.
Navigating the Courseware and Conquering the OSCP Labs
So, you’ve done the prep. You’ve got the basics of Linux, networking, and scripting under your belt. You’ve poked around in Virtual Hacking Labs, and now your PEN-200 start date has arrived. It’s game time.
In this second part, I’ll walk you through how I approached the official Offensive Security courseware, how I worked through the exercises and labs, and what strategies I used to stay organized, motivated, and on track to pass the OSCP on my first attempt.
Your First Week: Getting Comfortable with Kali and the VPN
When you receive your welcome email from OffSec, you’ll get access to the PEN-200 PDF course guide, the videos, and your VPN pack for lab access. The very first thing I did was skim the PDF to see how much ground I’d need to cover. It’s a long document, around 800 pages, and packed with content.
I skipped the video series almost entirely. It follows the same structure as the PDF but lacks the same technical depth. Instead, I dedicated my study time to reading, experimenting, and documenting my work in a structured way.
During the first few days, I made sure I was 100% comfortable in Kali Linux. That meant customizing my VM layout, testing out basic tools like Nmap, Netcat, and Gobuster, and making sure the VPN was stable. There’s nothing worse than starting a scan or exploit and getting kicked off your lab connection because of a misconfigured network.
Working Through the Courseware: Slow is Smooth, Smooth is Fast
The PEN-200 material starts gently, covering the basics of Linux, Windows, and networking. But don’t let that fool you, it ramps up quickly. You’ll move through buffer overflows, web app attacks, file transfers, privilege escalation, tunneling, Active Directory, and more.
The best way to go through the course is to approach it like a college class. I split the content into sections and gave each a deadline. For example, “Finish Linux Buffer Overflows by Friday,” or “Spend the weekend on web attacks and Burp Suite.” Having time-boxed goals helped prevent burnout and procrastination.
Sprinkled throughout the PDF are exercises. These range from simple “run this tool” tasks to challenges that require additional research and experimentation. While they’re marked as optional, I strongly recommend doing them, especially if you’re planning to submit the bonus documentation.
I tracked everything in a local Markdown-based note-taking system. Each topic had its own file. Inside were screenshots, commands, explanations, and links to additional reading. By the end, I had my own custom playbook of techniques that I could reference at any time, including during the exam.
Should You Do the Exercises and Bonus Lab Report?
This is a hotly debated topic in the OSCP community: should you spend time completing all the exercises and submitting the lab report for five bonus points?
Here’s my take, yes, it’s worth it.
You can earn five extra points on your exam if you:
- Complete all exercises in the PDF (with documentation).
- Root 10 lab machines and document them in the lab report.
While it’s a lot of work, I treated it as part of the study process. By writing everything down, I found I was retaining the material better. Plus, it forced me to move slowly and understand why things worked, not just how.
It’s not flashy work, but it builds your technical muscle and gets you in the habit of writing clean, clear walkthroughs – a skill you’ll absolutely need on exam day.
The Lab: Where the Real Learning Happens
The PEN-200 labs are where everything starts to click. This is your sandbox, your chance to take everything you’re reading and put it into practice.
The lab contains a series of networks. You’ll begin with the public network, and from there, you’ll compromise multi-homed machines that give access to internal networks. This teaches pivoting and lateral movement, which is critical to understanding real-world penetration testing.
You’re not given anything other than IP addresses. From there, it’s up to you to enumerate the machines, discover services, exploit vulnerabilities, escalate privileges, and document your steps. No hints, no walkthroughs.
At first, it’s intimidating. I remember staring at my terminal after scanning a target and thinking, “Now what?” But that’s the point. The labs are about problem-solving and pattern recognition.
Tools I Used Daily in the Lab
Here’s a non-exhaustive list of tools that became part of my daily workflow:
- Nmap for initial scans, OS detection, and service enumeration.
- Gobuster or Dirb to brute-force hidden directories.
- Netcat for simple shell access and port listening.
- Enum4linux, CrackMapExec, and smbclient for enumerating SMB shares.
- LinPEAS, WinPEAS, pspy, and GTFOBins for privilege escalation.
- Burp Suite for web app testing, intercepting and modifying HTTP requests.
The key isn’t just knowing how to use these tools, but knowing when to use them and how to interpret their output. That takes practice, and the labs are the best place to get it.
How I Documented Every Hack
Documentation is everything in OSCP. From day one, I wrote down every action I took, every command I ran, and every mistake I made. Not only did this help with learning, but it also ensured I was ready to write a solid exam report when the time came.
For every lab machine, I kept:
- A high-level summary of what worked.
- Enumeration output (Nmap, Gobuster, SMB enum).
- Exploitation steps with command history.
- Privilege escalation paths and tools used.
- Screenshots showing flags or proof.
- A timeline of how long each phase took.
If you’re doing the bonus lab report, this will save you massive time later. If you’re not, it still becomes an invaluable resource.
Lab Strategy: Build Momentum Early
I didn’t try to “save the hard ones” for last. I started attacking every machine I could access and built confidence from low-hanging fruit. The more I rooted, the more tools and tricks I learned. Over time, I started to recognize common misconfigurations and patterns.
By the end of the second month, I had compromised most of the public network and two internal networks. The last few weeks were spent refining privesc paths and revisiting machines I couldn’t get the first time.
If you find yourself stuck, don’t be afraid to take a step back and review the basics. Sometimes a missed port or service is all that’s blocking you. Other times, it’s a rabbit hole you need to step out of. The labs are not only about technical skill, they’re about mindset.
Managing Burnout and Staying Consistent
The OSCP grind is real. You’re juggling work, life, and study. You will burn out if you don’t pace yourself.
My rule was simple: study every weekday, take Sunday off, and protect my evenings. I averaged four hours a day, sometimes split into chunks. I never studied past 9pm, and I never skipped more than two days in a row. Consistency beats intensity every time.
The Final Push: When Are You “Ready”?
After 90 days in the lab, I had completed:
- The entire PDF, with all exercises documented.
- Rooted 10+ lab machines for the bonus report.
- Gained access to multiple internal networks.
- Built a repeatable workflow for enumeration and privilege escalation.
- Written clear and organized notes for each machine.
At that point, I felt confident, not just because I had finished the labs, but because I could approach an unknown box, enumerate effectively, and problem-solve under pressure.
When you start looking at machines and saying, “I know where to begin,” that’s when you’re ready for the exam.
Surviving the 24-Hour OSCP Exam — Strategy, Mindset, and Execution
If you’ve worked your way through the PEN-200 courseware and conquered a big chunk of the lab machines, congratulations, you’re already doing what many never finish. But there’s one final boss you still have to face: the actual OSCP exam.
This is where everything you’ve learned and practiced comes together. It’s a unique test, and there’s nothing quite like it, no multiple-choice questions, no second chances. Just 24 hours of pressure, hacking, and pure problem-solving. In this part, I’ll break down how I approached exam day, how I managed my energy and stress, and what strategies worked best to get through all five machines and earn that pass.
What the OSCP Exam Really Looks Like
Let’s get this out of the way: the OSCP exam isn’t just another cybersecurity test. It’s a mental and technical marathon – a 24-hour deep dive into your offensive security skills, followed by a report-writing session that can make or break your attempt. Success requires not just technical knowledge, but strategy, time management, and resilience. It’s one of the most respected certifications in the industry for a reason.
Overview of the Exam Structure
The Offensive Security Certified Professional (OSCP) exam gives you a single objective: gain root or administrative access to a series of machines and document your findings in a clear, professional report. It simulates a real-world penetration test. The exam lab environment consists of five target machines with various point values assigned based on difficulty and the type of exploit required.
To pass, you need 70 out of 100 points, plus up to 5 bonus points if you’ve submitted the PEN-200 (previously PWK) course exercises and lab report before your exam attempt. These points can give you a little buffer, but they’re not a guarantee, most candidates aim to score well above 70 to ensure success.
Let’s break down the types of machines you’ll likely face.
1. The Buffer Overflow Box (25 points)
This is often considered the “warm-up,” although it’s anything but easy for those unfamiliar with exploit development. You’ll be expected to identify a vulnerability in a custom application, typically a 32-bit Windows binary, and then craft a custom exploit using techniques like SEH (Structured Exception Handling), bad character avoidance, and shellcode injection.
You’ll use tools like:
- Immunity Debugger or GDB
- mona.py
- msfvenom
- Manual fuzzing scripts (usually in Python)
What’s being tested here is your understanding of buffer overflows at a low level, you must be able to analyze a binary, determine where it crashes, identify control over the instruction pointer, and inject your own payload. For many candidates, this is the box they prepare for the most, since it’s the most predictable. If you’ve practiced similar exercises in the lab or on platforms like TryHackMe or Hack The Box, you’ll be better positioned to tackle it.
2. Initial Foothold + Privilege Escalation (20 points)
This machine tests your ability to enumerate thoroughly, identify a remote code execution (RCE) vector, and then escalate privileges to root or SYSTEM. Typically, this is a Linux box, but it could be Windows. You’ll likely exploit a vulnerable web app, a misconfigured service, or an outdated CMS/plugin to get a shell.
Once you have low-privilege access, the fun begins. You’ll use tools and scripts such as:
- LinPEAS, LinEnum, WinPEAS
- Manual checks of cron jobs, sudo permissions, SUID binaries, and misconfigured services
- Kernel exploit research for local privilege escalation
- Password reuse or credentials left in configuration files
This box emphasizes the importance of basic enumeration skills and knowing what to look for post-exploitation. Many candidates lose points here not because they couldn’t get in, but because they didn’t follow through all the way to root.
3. Two Medium-Difficulty Boxes (20 and 10 points)
These machines will be similar to what you’ve seen in the PEN-200 lab environment. They usually involve one or more vulnerabilities chained together, like:
- Subdomain enumeration leading to a vulnerable service
- File upload bypass or local file inclusion (LFI)
- Credential reuse, weak permissions, or exposed database credentials
- Exploiting outdated versions of software or known CVEs
The 20-point machine might be trickier to enumerate or require more steps, while the 10-point machine is generally more straightforward but might include a curveball to throw you off.
What’s critical here is your ability to stay organized:
- Take thorough notes in real time
- Keep track of what ports and services are running
- Use automated tools like nmap, gobuster, ffuf, and nikto, but don’t rely solely on them, manual testing is key
Candidates who struggle on these boxes usually fall into the trap of rabbit holes or skipping enumeration steps. OSCP rewards thoroughness and patience.
4. The Hard Box (25 points)
The final machine is the most difficult and will likely combine multiple layers of complexity. This could be:
- A multi-user environment requiring lateral movement
- A machine with an intentionally confusing rabbit hole
- A realistic Active Directory setup with misconfigurations
- Chained exploits with misdirection and dead ends
Expect to spend several hours on this one. It might feel like hitting a wall if you’re fatigued, so plan your time wisely.
This box tests your deep understanding of the entire attack lifecycle, from recon and initial access to post-exploitation, enumeration, and lateral movement. It often separates those who pass from those who nearly make it.
Strategy for Tackling the Exam
Time Management is Everything.
You have 24 hours to work on the machines and an additional 24 hours to submit your report. A commonly recommended breakdown is:
- First 10-12 hours: Hit the 3 easiest machines first (BOF, 20-point, 10-point)
- Next 6-8 hours: Work on the remaining boxes (the harder ones)
- Final hours: Re-check footholds, grab screenshots, clean up notes, and make sure you’ve captured everything for your report
Note-Taking Is Not Optional.
You must take detailed, step-by-step screenshots and command logs showing how you exploited each machine. Missing a key screenshot can result in zero points for that box, even if you got root. Tools like CherryTree, Obsidian, or even plain Markdown files can help you stay organized.
Stay Calm Under Pressure.
It’s easy to panic when you get stuck. That’s where your training, lab experience, and mindset come into play. Take breaks, step away for 10-15 minutes, and come back with a fresh perspective.
The Report: Your Final Test
After the 24-hour exam window, you’ll have another 24 hours to submit a professional penetration test report. This document should include:
- The methodology used
- Screenshots of key steps (initial access, privilege escalation, proof.txt flags)
- Clear, organized explanations for each vulnerability and how it was exploited
- Remediation suggestions (optional, but adds polish)
This isn’t just a formality, it’s a real part of the exam. Offensive Security places a high value on your ability to communicate your findings clearly and professionally. You could technically root four out of five machines and still fail if your report doesn’t show proof or follow proper structure.
Getting root or administrator access is key. Partial credit is sometimes given for user access or foothold only, but it’s much safer to aim for full control.
The Day Before: Final Checks and Mental Prep
The day before the exam, I did zero hacking. No labs, no review, no late-night Googling. Instead, I focused on prepping my space and clearing my mind. I:
- Backed up all my notes and scripts
- Downloaded my OSCP exam template and checklist
- Prepped meals and drinks for the next day
- Slept early (seriously, don’t skip this)
Mental energy is your most valuable resource during the exam. You’ll burn out fast if you go in already exhausted.
Starting the Exam: Calm, Focused, and Methodical
Your exam portal will open at the exact time you selected during scheduling. Once you’re in, you’ll get the exam guide with rules and the IP addresses for the machines. VPN setup should only take a few minutes if you’ve done it before in the labs.
Once connected, take a deep breath and run an initial Nmap scan on all five targets using a wide port range and service version detection. Save this output. I always redirected it to a file for reference later.
My goal in the first hour was to:
- Run Nmap scans for all targets
- Label each machine (e.g., Target1, Target2…)
- Identify low-hanging fruit to prioritize
I used a checklist for each box:
- Enumeration: ports, services, versions, web content
- Exploitation: foothold or vulnerability
- Privilege escalation: local enumeration, known privesc paths
- Documentation: screenshots, commands, flags
The Buffer Overflow Machine: Start Here
The buffer overflow box is often the most straightforward for those who practiced this during the course. You know exactly what it’s testing, and you can prepare a skeleton script in advance. You’ll need:
- A vulnerable service listening on a port
- Immunity Debugger
- Mona.py for generating patterns and offsets
My strategy was to do this box first and get the 25 points secured early. It took about 2.5 hours from start to root, including testing my payload and confirming the shell. That’s a great confidence boost for the rest of the day.
Tackling the Other Machines
After buffer overflow, I turned my attention to the 20- and 10-point boxes. These are often web-based or have tricky initial access vectors. Here’s how I approached them:
1. Enumeration, enumeration, enumeration.
The OSCP is all about discovering what’s hidden. I used tools like:
- Gobuster and Dirsearch for directory brute-forcing
- Nikto for basic web scanning
- Nmap scripts for SMB, FTP, and SSH probing
2. Keep your cool.
More than once, I thought, “There’s nothing here.” But with persistence, trying a different user agent, tweaking a URL parameter, or just reading a robots.txt file, something always opened up.
If you hit a wall for more than 90 minutes, move on. It’s better to have multiple partials than burn five hours on one dead end.
Privilege Escalation: Where Many Fail
Getting a shell is one thing. Getting root or SYSTEM is where the real points are.
For local privesc, I used:
- LinPEAS/WinPEAS to identify weaknesses
- Manual checks: SUID binaries, writable paths, services running as root
- Cron jobs, PATH hijacking, and kernel exploits
I always ran enumeration scripts and saved the output for review. Sometimes you’ll miss something obvious until you reread it an hour later.
On one box, I escalated by abusing a misconfigured service that let me modify a startup script. On another, it was a writable cron script running as root every minute.
Staying Sane Over 24 Hours
This test isn’t just about skill. It’s about endurance. I treated it like a long shift at work—structured, but with breaks.
Here’s how I managed time:
- 0–6 hours: Buffer overflow + easiest box
- 6–12 hours: Two mid-range boxes
- 12–16 hours: Hardest box or revisit missed privesc
- 16–20 hours: Polish documentation
- 20–24 hours: Sleep or short rest (I took a 2-hour nap)
I scheduled breaks every 3 hours. Got up. Stretched. Walked around. Ate something. This helped me reset mentally. You don’t want to hit hour 18 with fried nerves and no working shell.
Real-Time Documentation: Don’t Wait
Document your steps as you go. Take screenshots of every shell, flag, and critical step. Write down exact commands. If you forget, you can’t go back after the VPN shuts down.
I used a local Markdown template for each machine:
- Target IP and name
- Steps to gain access
- Exploit details and commands
- Privilege escalation method
- Proof.txt and root.txt flag locations
By the time I finished a box, I already had 80% of the report written for that machine.
Submitting the Report: Last Step
After the VPN session ends, you have another 24 hours to submit your exam report. I didn’t wait, I wanted to be done. I polished my documentation, double-checked everything, zipped up the report, and uploaded it to OffSec’s exam portal.
Make sure your report:
- Has clear steps with screenshots
- Includes the required headers and format (follow their template)
- Covers each machine you rooted or partially exploited
- Includes the bonus points report if you’re submitting it
Don’t forget to test your ZIP file and double-check file naming before submitting.
The Wait: 5 Business Days of Stress
Waiting for the results was rough. Every day, I checked my email a dozen times, refreshing like I was waiting for college admission results. On day five, I got the email.
I passed.
The mix of relief, pride, and exhaustion hit all at once. I had done it. I had passed one of the most challenging cybersecurity exams in the industry.
Key Takeaways from the OSCP Exam
- Start with what you know: Knock out the buffer overflow first and get some early wins.
- Keep moving: Don’t get stuck in one box for hours. Time is your enemy.
- Document everything: Your report is half the battle.
- Stay calm: You’ve trained for this. Breaks are as important as brute-forcing directories.
- Respect the challenge: This isn’t just about hacking. It’s about thinking like a penetration tester and proving you can operate under pressure.
What Happens After OSCP — Career, Confidence, and Continuing the Journey
So, you’ve put in the hours, dealt with the frustrations, hit those breakthroughs, passed the 24-hour exam, and submitted your report. Then after five long days of second-guessing everything you did, that glorious email hits your inbox — “Congratulations, you have successfully completed the Offensive Security Certified Professional (OSCP) exam.”
It’s hard to explain how satisfying that moment is unless you’ve lived it. But what happens next? Is it all sunshine and job offers? How do you keep the momentum going? In this final part of the series, I want to talk about life after the OSCP — what changed, what didn’t, and what you should consider for your next steps, both professionally and personally.
The Immediate Aftermath: Let It Sink In
Once I got the email, I closed my laptop and just breathed. It felt like something had shifted inside me. I had taken on one of the most respected certifications in cybersecurity and made it through on my first attempt.
But after the initial high faded, I hit a weird phase: now what? I had been laser-focused on the exam for months, and suddenly there was free time in my day again. No more scanning subnets or privilege escalation rabbit holes. Just… silence.
That downtime is important. You’ll need it to recover mentally and physically. So, take a break. Enjoy life a bit. Let the win settle in before planning the next step.
Updating the Résumé and LinkedIn
Within a few hours of passing, I updated my résumé and LinkedIn profile to include the OSCP. And, no surprise here, the profile views and recruiter messages went up almost immediately.
Cybersecurity is a competitive space, but OSCP still carries a ton of weight, especially for roles in penetration testing, red teaming, and ethical hacking. It shows that not only do you understand security principles, but you can actually apply them under pressure with zero handholding.
Here’s how I presented it:
Certifications:
- Offensive Security Certified Professional (OSCP) – Passed on first attempt
- Penetration Testing with Kali Linux (PEN-200) – Course Completed
Skills Highlighted:
- Exploit development
- Privilege escalation (Linux/Windows)
- Buffer overflow attacks
- Network and web application penetration testing
- Pivoting and tunneling in segmented environments
I also mentioned my OSCP experience in cover letters and applications. It gave me an instant edge, even for roles that weren’t directly pen-testing-related.
Career Impact: What Changed
Within three weeks of adding OSCP to my résumé, I landed multiple interviews — two red team positions and one hybrid blue/red SOC role. All three interviewers asked about my exam experience and how I handled the challenges. They wanted to know:
- How I dealt with roadblocks
- Which tools I leaned on the most
- What kind of post-exploitation tasks I performed
It became clear that OSCP wasn’t just a “checkbox cert.” It was a talking point and a way to demonstrate I could think like an attacker.
Even if you’re not immediately switching jobs, OSCP elevates your status inside your current team. I found myself being looped into more security-related meetings, asked to review vulnerability reports, and given the lead on more technical engagements.
Was It Worth the Cost?
Let’s talk dollars and ROI. The PEN-200 package I chose came in at $1599, which included 90 days of lab access and a single exam attempt. Add in maybe another $250 for supplemental resources like Virtual Hacking Labs and subscriptions to platforms like Hack The Box and TryHackMe.
So, roughly $2,000 total.
What I got back:
- Career momentum
- More interview opportunities
- Better compensation negotiations
- Confidence to tackle real-world problems
Within a couple of months, I had a job offer with a $15,000 salary bump directly tied to my OSCP skills and practical knowledge. So yeah, I’d say it paid off big time.
Continuing the Journey: Don’t Stop at OSCP
Passing OSCP isn’t the end, it’s the start of something bigger. Once I finished, I found myself hungry to learn more. There’s still so much I don’t know, and the exam opened my eyes to areas I wanted to get stronger in.
Here are a few things I did next:
1. Tried Harder, the Smart Way
I kept hacking on Hack The Box and TryHackMe, but with a more strategic mindset. Instead of just popping boxes, I focused on learning why something worked. I practiced using fewer tools and more manual techniques. My goal was to master the process, not just the outcome.
2. Studied for OSWE and OSEP
OffSec has more advanced certifications, and after OSCP, the OSWE (focused on web application exploitation) and OSEP (advanced pentesting and evasion) both caught my interest. I’m currently working through the material for OSEP, and the OSCP foundation has made that possible.
3. Contributed to Community Projects
One of the coolest parts of this journey was giving back. I started writing up walkthroughs (without spoilers) and contributing to Discord communities where new OSCP hopefuls gather. You don’t realize how much you’ve learned until you teach someone else.
4. Used Exam-Labs for Theory Refinement
Although the OSCP is highly practical, I didn’t want to neglect the theory and fundamental concepts. I used resources like exam-labs to go deeper into topics like network architecture, secure coding practices, and red team tactics. It helped fill in some of the knowledge gaps that I missed during the heavy hands-on focus of OSCP.
Lessons I’ll Carry with Me
Passing OSCP taught me a lot more than how to exploit a vulnerable web server or write a reverse shell in Python. Here are a few life lessons I picked up:
Persistence > Perfection
No one aces every machine. You’ll get stuck, frustrated, and angry. But if you don’t quit, you’ll find a way forward.
Documentation Matters
Whether in the exam or the workplace, clear notes, screenshots, and structured reports make all the difference. It’s a skill that translates well across security roles.
Time Management is Everything
The OSCP forces you to prioritize. That skill alone helps with every project and job I’ve taken on since.
Community is Underrated
The OSCP community online is incredibly helpful. Discord channels, subreddits, and forums like NetSec students helped me stay motivated. Find your crew, share your journey, and lift each other up.
Is OSCP Right for You?
Let’s get real: OSCP isn’t for everyone. It’s grueling. It will test your patience, your critical thinking, and your ability to work in complete silence under pressure.
But if you want to be taken seriously as a penetration tester, security analyst, or red teamer, it’s one of the best ways to prove your value.
Ask yourself:
- Do I enjoy problem-solving more than reading theory?
- Can I commit to hours of independent study?
- Am I okay with failing and trying again?
If yes, then OSCP might be your next great leap.
Final Thoughts: From Fear to Confidence
Before I started OSCP, I felt like an imposter in the security world. I’d been around systems, knew some scripting, and dabbled in vulnerability scanning, but deep down, I doubted whether I really “belonged” in infosec.
Now, after passing the exam, I’ve changed.
I think differently. I approach problems like a hacker. I speak with confidence in meetings. I know I earned my spot in the field. And you can too.
One Last Word
If you’re thinking about starting the OSCP or are deep in the middle of it right now, just know, it’s okay to be overwhelmed. It’s okay to take breaks. What matters is that you keep pushing. The skills you build and the mindset you develop will stay with you forever, long after the flags have been captured and the exam has been passed.
You’re not just learning how to hack.
You’re learning how to solve problems, build resilience, and grow into the kind of cybersecurity professional companies want on their team.
