My OSCP Journey

Like everyone else, I also wanted to complete my OSCP in a short period of time. I successfully completed my OSCP exam in 3.5– 4 hours. However, since I completed my OSCP with a Mac M1, I faced a lot of issues. I’ll share insights from that perspective as well. In this blog, I’ll share my journey, pathways, and my preparation guide. At the end of the blog, I’ll also share the machines I’ve completed and my notes.

When I begin my career in cybersecurity, I want to do many things like RF/SDR hacking, red teaming, reverse engineering, and so on. One item on my bucket list is the OSCP certification. Initially, I planned to complete my OSCP within 3–4 years. However, after receiving guidance from my friends, I decided to complete the OSCP within 2 years. Thankfully, I am in an environment where I need to push myself very hard. My end goal with certification is equip myself for red teaming and Incident detection.

I received a voucher for the OSCP from my organization, thanks to my senior manager and one of my college junior who believed in me every step of the way, not just in my projects.

First month of preparation:

Over the course of three months of preparation, with the help of my brother Dinesh Chelladurai, I began by completing the labs and submitting flags and also started to work on Hackthebox. In the initial first month, I completed around 20–25 boxes from Hack The Box, where I learned about the basics. Since I worked under pressure, I spent only 5–6 hours per day.

Second month of preparation:

I was managing multiple projects simultaneously, which required me to push myself to the limit. Even with a packed time, I dedicated my mornings from 9 am to night until 11:30 pm to my office work. After getting some rest, I started studying for the OSCP from 12:30 am to 4:30 am at night during my second month. This routine continued for the second month, during which I completed Medtech, Reila, and OSCP-a. At the end of the second month, I completed around 40–50 boxes from Hack The Box, Proving Grounds, and TryHackMe, where I learned about different methodologies.

Final month of preparation:

Now, the main game begins. I started taking leaves to focus. I created several Burp extensions and automation tools with Python, PowerShell, and Bash, automating almost every workflow in my office projects while maintaining high-quality delivery. I dedicated myself to preparing for my OSCP exam, studying for 16 hours a day. In the last month of preparation, I completed Skylark, OSCP-B, and OSCP-C within 15 days. After that, I began working on Hack The Box, Pentester Academy, TryHackMe, and VulnHub machines as well.

At the end of the preparition of whole three months. I’ve almost completed around 200+ machines. Here you can find the list of machines I’ve completed.

Exam Day: — Its not about the exam its about the process!

With the motivating words from my friend, I began the exam.

1. Active Directory:

On exam day, I completed Active Directory (AD) within one hour. The only place where I got stuck was transferring files. The new Windows Remote Management (WinRM) wasn’t working sufficiently for transferring files from my Kali machine to MS02. So I took an alternative approach for transferring files by using an older version of WinRM. Since I already have a bonus point, I have now pwned Active Directory. So now I have 10 + 40 marks. Here is where my second month of preparation helped me a lot, where I used multiple methodologies, even for transferring files.

2. Standalones:

For standalone machines, it’s pretty straightforward; those are similar to Practice Ground (PG) machines. So, for each machine, it took 45 minutes to 1 hour. Within 3.5 hours, I got a passing mark, and I pwned the last machine within 30 minutes using the same methodology. Now I have 10 + 40 + 20 + 20 + 20 = 110 points. I now have a bit more confidence in my knowledge.

Take away:

After the exam, I understood the flow; it’s all about the methodology. If you get stuck somewhere, it’s important to know how to proceed further. Also, please keep in mind that the exam machines and lab machines are intended for hacking, so don’t lose your hope until the last hour.

Comparing practice machines with exam machines:

I encountered an Active Directory setup similar to one of the Vulnhub machines, and other standalone machines were similar to Pentester Academy machines and OSCP labs. Since I started my OSCP journey with guidance from a few friends, I took notes at each step and method. I performed multiple methods for each vulnerability. Those manual methods from oscp labs helped me a lot.

Since I took my exams, labs, and everything on ARM architecture, I faced many issues. I used Parallels for running a Kali virtual machine. I collected and shared tools specifically for the Mac M1, especially for the OSCP exam, on a GitHub page. Please feel free to grab them.

Result:

After the exam, I waited for almost three days to receive the result. Yes, I completed my OSCP within a short period of time. I was so happy. Thanks to everyone who supported me throughout the journey.

Here you can find all my notes from this OSCP journey. I hope you guys learnt something new here. Feel free to hit me up on LinkedIn, if you have any questions or concerns.

In my next post, I’ll share my own Burp plugins and some of my interesting findings.

Follow-ups:

1. Finding a study partner on Discord groups or Reddit can be incredibly beneficial. Working together keeps you motivated and accountable. I highly recommend joining study groups and finding a study partner.
2. Don’t push yourself too hard, guys. If you are planning for OSCP, try to spend dedicated hours, like 3 hours per day. I made a mistake during my learning time; since I spent too much time on work and learning for OSCP, I became exhausted and frustrated. It’s okay to take a break.
3. It is ok to give up in between. But the main thing is we can start again
4. Always take detailed notes during your studies.
5. Use different methodologies and tools for each vulnerability you encounter.
6. Try to automate simple workflows wherever possible.
7. Practice on as many machines as you can. The exam is about building a methodology.
8. If you get stuck, it’s okay to refer to write-ups. The objective of the lab is to develop our methodology.
9. Seek guidance from peers and seniors. Discuss methodologies and tactics, techniques, and procedures (TTPs). I took help from so many people especially my friends and community members.
10. Try running the same methodology with different versions of tools, as sometimes issues arise with the latest versions.
11. Familiarize yourself with all different file transfer methods.

Certificate:

Way to go!

I’m planning to prepare for OSWE. If you’re interested, please reach out to me. Let’s start the preparation together.