Career Path Penetration Testing Basics

Penetration Testing – “A method for gaining assurance in the security of an IT system by attempting to breach some or all of that system’s security, using the same tools and techniques as an adversary might.” (From wikipedia)

The scope of the article is to help to get your first job as a penetration tester. If you have more great links or recommendations please add them in the comments section. Becoming a good penetration tester requires much more skills than described here. It also means that you never stop learning.

If you don’t know the IT- and IT security basics yet, please have a look here. When you want to start a career in Penetration Testing you should know that most of the penetration tests performed today are Web Application tests. Therefore this article is focusing on this topic. Later I will add new posts with Specializiation Paths for more advanced topics like exploitation, red teaming and so on.

As already mentioned in the article Career Path Security Basics, I strongly suggest that you make a plan what goal you want to reach. For example playing CTF all the time might be fun for some people, but if you need the OSCP it might not be helpful to waste too much time.

Web App Penetration Testing

Port Swigger: Web Security Academy
Content: Teaches the basics of Web Application Security, so far SQL Injection, XSS, OS command injection and File Path traversal. Comes with small labs.
Career: Penetration Test but I recommend it also for everyone interested in security
Level: Beginner
Price: Free

Recommended Link about Web App Hacking:

 

General

OSCP
If you want to start a career in Penetration Testing you might consider to make the OSCP certification. But you should have in mind that the OSCP is extremely time consuming and it is not a must have, but definitely a door opener. Therefore I recommend to do the OSCP certification. Here is an article about pros & cons of certifications.

Hands On

Here are some hands on for labs and learning. Some of them are online, others have to be installed and run by yourself.

Books

The Web Application Hackers Handbook
Authors: Daffy Stuttard, Marcus Pinto
Content: The standard book about hacking Web Applications, goes into depth about the most important topics. Authors also created the BurpSuit.
Career: Penetration Tester
Level: Good for beginners, but also useful for experienced penetration testers
Buy at Amazon U.S.
Buy at Amazon Germany

Penetration Testing: A Hands-On Introduction to Hacking
Author: Georgia Weidman
Content: A great introduction into penetration testing.
Career: Penetration Tester
Level: Beginner
Buy at Amazon U.S.
Buy at Amazon Germany

Metasploit: A Penetration Tester’s Guide
Authors: David Kennedy, Jim O’Gorman, Devon Kearns, Mati Aharoni
Content: Introduction to Metasploit and penetration testing
Career: Penetration Tester
Level: Beginner, Intermediate
Buy at Amazon U.S.
Buy at Amazon Germany

The Hacker Playbook 2
Author: Peter Kim
Content: Book for penetration testing, hands on hacking, pivoting, evasion and so on. 
Career: Penetration Tester
Level: All
Buy at Amazon U.S.
Buy at Amazon Germany

Network Security Assessment
Author: Chris McNab
Content: Assessment of various network services.
Career: Penetration Tester
Level: All
Buy at Amazon U.S.
Buy at Amazon Germany

German Book: Hacking mit Metasploit
Author: Michael Messner
Content: Great introduction to penetration testing and metasploit.
Career: Penetration Tester 
Level: Beginner/Intermediate
Buy at Amazon U.S.
Buy at Amazon Germany

Links

Thanks @SparkyS04 for proofreading.

Certifications Pro & Con

A lot has been written about certifications and whether you should have them or not. For me it is pretty simple, certifications helped me finding jobs and improving my career.

As a penetration tester I made OSCP and OSCE, for getting a bit more into DFIR I made the CHFI certification. At the beginning of my career I did CompTIA Network+ and Security+ for learning and prooving my skills. At some companies it is simply a door opener. I know enough people who never certified and are great at their jobs and also don’t have problems making a good career.

But of course there are other ways to show your motivation:

  • have projects or a blog that are showing your skills
  • have you found vulnerabilites? write them down in your CV
  • found something great? consider to give a talk at a conference
  • maybe you are a great CTF player?
  • don’t forget your personal network

Besides that, what certification you want to do strongly depends on your career path and the budget. SANS courses & certs cost a ton if you have to pay for yourself and are mainly useful if you want to go into DFIR.

On the other end there are certifications from EDX or coursera that are cheap but of course not that recognized. Certifications from securitytube are also worth a look.

After all it is the mix of certifiations, courses, experience, personality, connections and so on that enables your career.

Getting started with hackthebox

Career Path, Labs: Penetration Tester
Challenges: Penetration Tester, Forensics, Malware
Level: All

Until now I never realized that hackthebox also offers free accounts, so I decided to test it and write a short post. 

After a challenge here you can create your login. With the connection pack for openvpn it is possible to connect to the labs with a Kali machine (or any other Linux I guess), easy.

With the free account you can solve challenges and active machines.

Active machines
For owning systems and users there are flags that are stored in files on the machines, for example:

The labs remind me about the OSCP labs, and lots of people are using them for training before the OSCP certification (which might be a good idea, though I did not) or to get an impression about the labs and the exam.

For more information and getting an impression about owning boxes look here, lot’s of walkthoughs for retired boxes.

At the time of this writing 20 machines were online, with different OS versions (Linux, Windows, BSD) and different scenarios. I had a closer look at some boxes and solved one so far in a couple of hours. 

The lab looks really fun, and I would recommend it for everyone who wants to train and learn hacking.

Challenges
The challenges also look quite good, i had a look but honestly, I am much more into owning. Here are the categories for the challenges:

For solving for example the Stego challenges, you download a file with a hidden message and have to find it. I was surprised that there are also some Forensics challenges, I will defilnetly have a look into those too.

Conclusion
This is definetly a great playground for everyone who is into solving challenges and pwn boxes. I am not sure if hackthebox is good for total beginners, there are no big explanations or tutorials for the machines or what is to do. There are the official forums with hints and some websites offering more in depth explanations, although the rules say that this should not be done, and somehow as an OSCP taker (“Try harder”) this feels like cheating. With the VIP membership you also have the retired machines with walkthroughs.

For your career hands-on and solving challenges is a very important part, so I recommend: sign up.

Links:
https://www.secjuice.com/hack-the-box-starter-pack-edit/
https://veteransec.com/category/hack-the-box-write-ups/
https://resources.infosecinstitute.com/hack-the-box-htb-machines-walkthrough-series-jerry/#gref

Start a Penetration Tester Career

This article is part of an article series about my personal experience and career in the penetration testing and security field.
Part 1: Start a Penetration Tester Career (this part)
Part 2: From Beginner to Expert as Penetration Tester
Part 3: Working at a CERT and shifting to Technical Lead

From Administrator to the first Penetration Tester Job

I am sharing this because people ask me often about how to get into information security and how to improve a career. In this post, I describe my personal career and learning path including recommendations for books and more learning material. This may not be perfect to other people, for me it just worked. In later posts, I will give some recommendations for a more idealized learning path for different careers, for example as a penetration tester or a forensics specialist.

When I was working as an administrator back in 2011, I began starting to think about how I might change my career. My job back then included some Windows and Linux administration as well as some PHP and VBA coding. Further, I had coding skills in C and Java. In October 2012 I started my first job as penetration tester.

At this time, it was not clear to me whether to go more into depth as a network admin or to security. Since it seemed to be a good idea to have some networking skills, I started to work out a plan for getting the CCNA. 

Network skills
I started with the Mikrotik MCNA, since there was a training possibility in the town where I lived, I only used the training material offered by this course, but if you want more information have a look at the official Mikrotik page: https://mikrotik.com/

Then CompTIA Network+ followed. For the test preparation, I relied on two sources. The first is the free video series from professor Messer, these are excellent and I used to make notes about the content and reviewed them before a new training session. After the videos, I bought the book
Mike Meyers’ CompTIA Security+ Certification Passport” that included some example questions for training.

The CCNA was my first “bigger” certification and I remember that I put a lot effort in it, for example I bought a bunch of old switches and routers for a home lab. This was not necessary, but of course, it added some fun at this time. Much easier is to use simulation software for doing some labs.

Besides my own experiments, I worked through the book CCNA Routing and Switching Complete Study Guide. The certification at this time included not only the multiple choice tests, but also lab exercises.

Security skills
Because it became clear to me that I wanted to go into Security in my career, I started the CompTIA Security+ certification. As like for Network+ I used the Professor Messer tutorials and the book Mike Meyers’ CompTIA Security+ Certification Passport. 

I wanted to work as a penetration tester; I decided to do the OSCP certification and I am happy I did choose it over the CEH. Here is my review in German, more reviews in English here.

I made the certification in 2012, and nowadays I do not think that you must have an OSCP necessarily, although I strongly recommend it. It is a great certification and it surely helped me especially when it comes to attitude, endurance and patience. However, it can be a frustrating experience and if you do not have enough time or motivation, it will be hard. For me it was fun!

During the OSCP preparation, I bought two books:
–      The German book “Hacking mit Metasploit” (Hacking with Metasploit) by Michael Messner, which helped me a lot because it also introduced some Exploit Development and Client Side Attacks.
–      Hacking: The Art of Exploitation by Jon Erickson 

After the OSCP, I was lucky to find my first Job as a penetration tester.

Besides the certifications I also did a course at coursera “Webapplication Engineering” which I liked but it seems it was not continued.

Together with a friend we published an article in the German issue of the pentest magazine about pivoting, which was good having it on my CV for the first job in the field.

Conclusion
If you want a job in this field, the most important thing for me is to show that you are motivated. Nowadays I had some job interviews “on the other side” from the perspective of an employer. So besides qualifying with certifications and courses you should consider:

  • Start your own blog
  • Start your own projects on github
  • Contribute to projects
  • Networking (when I looked for my first job as a penetration tester I used Xing and wrote to company owners and asking for a job, which was successful) 
  • Consider publish articles on platforms like Xing, LinkedIn, magazines etc.

In the next part, I will go from starting the first job to going for expert level.