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This sharing entails about the journey (in bite size!) of my Penetration Testing career, there may be useful information and inspirations that you may obtain, especially if you are an individual interested in enteringo the Penetration Testing domain.

The Question

Since young (199x~Current), I have had the opportunity to witness how technology advances rapidly within a short 20-30 years. One question that has constantly been on my mind is:

If technology advances so quickly – the birth of applications, software, hardware, websites, etc. gets obsolete extremely quickly, what is the one component of this advancement that always stays the same? In other words, how do I stay relevant in this ever-changing field of Information Technology?

My answer to that is: Cybersecurity. This thought eventually placed me on the journey of Cybersecurity and here is how i started.

Background

I come from a background with the following qualifications:

• Diploma in Info-comm Security Management
• Degree in Information Systems and Management

As there are a wide array of different domains and roles of Cybersecurity such as:

• Offensive Security / Red Teaming
• Defense Security / Blue Teaming
• Network Security
• Incident Response and Forensics
• Governance, Risk Management, and Compliance (GRC)
• Security Operations (SecOps)
• and more!

I have decided to embark on the Offensive Security domain, as likewise with most of the fellow Offensive Security readers, it’s cool!

Technical Proficiency

Since I started with only very fundamental knowledge of Cybersecurity, these are the following resources that I utilized that were extremely useful to start with:

1. TryHackMe

TryHackMe was a valuable partner and mentor during the start of my journey. The lessons and labs are easy to understand and organized in a very bite-sized format. As with any penetration testing methodology, the most important phase is enumeration and reconnaissance. I started learning important reconnaissance tools and concepts from the lessons and labs and even basic exploitation of simple misconfigurations and vulnerabilities that really got things going!

2. Live Experience

During the learning phase, I was very fortunate to have obtained an opportunity to become a trainee for an Offensive Consultancy company and had hands on experience to perform and take part in projects that allowed me to learn Vulnerability Assessment and watch how Penetration Testing should be done. Furthermore, I had really great colleagues – shout out to Jerry and Edmund, who had been really generous with their knowledge and assisted me to overcome obstacles during my projects.

3. eLearnSecurity Junior Penetration Tester Certification

After having hands-on experience for quite a while and also learning new skills on TryHackMe, I have attempted the EJPT certification and obtained it successfully. For more information on this certification, you can check out the EJPT Exam Review here.

This is a great certificate that serves as a fundamentals validation and confidence boost!

4. OSCP (Offensive Security Certified Professional)

OSCP is one of the most recognized Penetration Testing Certificates internationally and the reason for that is – it is extremely difficult.

I had took a period of 4 months to prepare for the examination. This period features countless of late nights and sanity checks that newcomers best be prepared for!

During this period, it is extremely helpful to have a partner/friend, you are able to discuss about exploitation techniques, methodology, tools and useful commands that can make this whole process more efficient and enjoyable. Shoutout to Darren for walking this journey with me! (All the best for OSWE 😛 )

Attaining OSCP is one of my most important milestones as a Penetration Tester and the most important thing that I have learnt is – Try Harder. (Also their motto!)

Some takeaway are:

1. Always know multiple ways to do the same thing. It can be file transfers, enumeration, bruteforcing, privilege escalations, etc.
2. Always have a strong and comprehensive methodology that you can follow step-by-step. It is very important to have this as under pressure you may not remember every single thing that you can check for and sometimes the vulnerability is right in-front of you!
3. Good reporting habit – Having a good habit for reporting format and evidence taking takes a lot of pressure off during the exam.
4. Searchsploit is your best buddy!
5. Practice and Practice! – I have done more than 100 labs during my preparation from TryHackMe, HacktheBox and Proving Grounds(recommended!).

For more information on the exam preparation and exam day, you can check out the OSCP Exam Review here!

Summary

At this point, you are already a qualified Penetration Tester! A great recommendation after OSCP would be to obtain Web Exploitation and Source Code Review skill-set via Portswigger and OSWE certification.

Always remember, skills and concepts can be learnt and what you don’t know about today, can turn into your strength tomorrow if you tackle it and overcome it!

All the best on your endeavors!