Life as a pen tester after the PWK / OSCP

This is my personal experience of what happened after passing the OSCP exam.

I passed the OSCP, applied to a bunch of positions, went on a bunch of interviews, and after some time, became a red teamer. I am now a penetration tester with Leidos, and so far, I enjoy it.

Post Exam
I have noticed a lot of people posting blogs after taking the OSCP exam. A lot of them have been pretty good articles about their trials and tribulations in relations to the PWK course and subsequent OSCP exam. It’s great to see many others being successful in the OSCP exam and achieving their certification.

What I have also noticed is that not many people post a whole lot about their experiences after obtaining their OSCP. This article will be about my life post OSCP.

Searching and searching
A little after I passed the OSCP exam I updated my resume and my LinkedIn profile. At that time the OSCP wasn’t as well known to people as it is today. Kudos to Offensive Security for getting their name out there and making more people aware of what they provide. Not only just training, but also their security services. I had a few recruiters sending me messages about various positions. Mostly junior security positions. At that point of my career, I already had 20 years of IT experience, and a year and half into security engineering. So I was not looking for a junior position. I knew what I wanted, I was comfortable in my position, and was willing to wait until I found the right position that was right for me.

It took a year before I landed in the right position. During that year I went on countless interviews, including one within my own company (Lockheed Martin). I even landed an interview because of my article on my PWK/OSCP experience. Nothing was what I wanted. In the mean time while I was searching I was trying to keep my skills sharp. So I started working on more vulnerable machines from vuln hub, I was reading more security related articles, and getting more on /r/netsec.

Great success!
Eventually I found a great position for a government red team. I wasn’t sure I was going to be able to do it, as I hadn’t ever done any penetration testing for a company at that point. I thought to myself, what the hell? The worst that’ll happen is I’ll get the job.

So I applied, and I got a call back the next day from the recruiter. He wanted to talk about salary, and tell me a little more about the job etc. A couple of days after that, I had a technical interview with someone at the company. The screen went very well, and I was able to show them I was passionate about security and was knowledgeable about penetration testing. They wanted to bring me in for an on site penetration test in their lab, but the lab was down. I was happy to do the on site test if it were available. So instead I told them I would take a PC recording of me attacking a vulnerable machine, and the steps needed to enumerate etc. They liked the idea. So I did the task, and sent it over to the person I had spoke to. They liked what I had done,  and after an in person interview with the same person, and their management, they offered me the position.

I really enjoyed that process because it put me on the spot to perform and provide a deliverable, and in doing so rewarded me with a position on a red team. Not bad for someone who had no penetration testing experience.

I enjoyed my time with that particular red team. I learned a lot and got to do some really cool things. I got paid to hack government computers, and not go to jail! How cool is that?

To infinity and beyond!
Like all good things, everything comes to an end. The missions dried up, and I wasn’t getting any training. I wasn’t really looking for another opportunity, but my current position came up and was presented to me. I decided why not listen to what they had to say? I went to an interview and did well. I was offered the job with more money, and promised training. In addition they’d send me to defcon. After a couple of days of thinking, I decided to take the job. This new position is providing me with different challenges and I am learning. You can’t really beat that. I’m hoping to stay here for a few years, learn some more, and provide a valuable service to my customer.

About me
I have a BS and MS in IT/Cyber security and I have a whole bunch of IT certifications (MCSE, MCSA, RHCSA, VCP, CEH, GCIH, OSWP, OSCP).
I also have over 20 years of IT and security experience, and I am a Navy veteran.
I’m sure that my sheer drive and determination lead me to where I am today. Never stop learning, and always keep pursuing  your goals.

In the immortal words of conner4real: Never stop never stopping.
OSCP Never Stop Never Stopping

Try Harder! My Penetration Testing with Kali Linux OSCP Review and course/lab experience

Try Harder! My Penetration Testing with Kali Linux OSCP Review and course/lab experience — My OSCP Review

Obtaining the OSCP certification is a challenge like no other. After my experience with the OSCP exam and course from Offensive Security, I decided to go ahead and write an OSCP Review. I decided to take the OSCP course and exam in September 2014 after seeing some fellow members of a forum I frequent quite a bit ( state that they were taking it soon. This is a course and exam I wanted to tackle as I have a passion for IT security. I figured why not sign up as the same time and compare notes etc with like minded people, and make the process easier.

So I signed up, for the 90 days, and a week later, I was sent the introduction email with all the information I needed to connect to the Offensive Security labs via VPN, IRC information, login information, and forum information.

About me:
I have about 20 years of combined IT experience. I have two MCSEs, two MCSAs, MCITP:VA, VCP5, Security+, CEHv7,  RHCSA, a BS in IT security, and I am finishing up my Masters in Applied IT with a concentration in Applied Cyber Security.  I currently work for Lockheed Martin as an Active Directory Engineer on a government contract.

The course:
When I first signed up for the course, I quickly went through the manual and videos that included with the email once you start the course. A lot of the information I was already familiar with as I had to review a lot of it for the CEHv7 certification. As we all know the OSCP exam and course are very technical and very hands on. The CEH is pretty much all about theory and multiple choice questions. I was glad to take a course that not only talked about tools, but how to use them, and why they are used.

So when I first started the course, I was very motivated. The very first day I was in the labs, I was able to knock out 3 servers with very minimal effort. At this point I am thinking to myself, this is too easy! That is, until I met “sufference”. Over the course of the next month or so I was able to get to about 20 servers. As I said in the beginning I was super motivated, but as time goes on, I was losing interest, and just simply didn’t have the time.

As I said, I thought I this course was too easy at first, and I was able to knock out server after server. That is until I met sufference. This is where I lost a lot of motivation. I believe I spent 3 weeks alone on this beast of a server. It demotivated me and made me feel like a child who just had his ice cream money stolen by Vic the bully down the street. I spent hours a day on this server alone obsessing over it. I decided to come back to it. So I move on to some other challenging servers and I am able to root them and get some of my confidence back.

I decide to go back and kick sufference right in the teeth after this. I do a lot of googling, AND I MEAN A LOT, and finally I find a way in and get a limited shell! Great! Half the battle has been won! This is not enough for me, I need to make this server my bitch and show it who’s boss. Yeah… not so much. Again I decide to regroup and move on…. maybe the answer will come to me. I pop a few more servers (at this point I am close to my 90 day point. I HAVE TO OWN THIS BEFORE MY LAB TIME IS UP!  One more attempt I tell myself.

I finally come across something that clicks for me, and I have one of those AH-HA! moments. Its something I should have seen sooner… but for some reason I did not, and stayed ignorant. I finally found the answer, and I was able to root sufference after nearly 3 months! My motivation and confidence have been renewed.


I decide to extend for another 30 days. I only have about 30 servers owned at this point… and I hadn’t unlocked any of the other networks. I can do better. So I renew and I decide my new goal is to at least get into the admin network. After a lot of time spent in the labs and researching exploits etc, I had finally learned how to pivot into the admin network. Thank you proxy chains! I was able to get all of the servers in the IT network, and all but one in the admin network. My time was almost up in the labs, so I decided to go ahead and book the exam. I felt I was ready and could do this.

The Exam (part 1):
The exam is a 24 hour challenge. This means that you have 24 hours from the time the exam starts to try and compromise the servers assigned to you in the exam. Additionally you have another 24 hours after that to write your report and send it in for grading. You are graded on your report alone, and you HAVE to complete this in order to pass the exam. You are also encouraged to submit a lab report documenting your efforts in the lab. You may get extra points for this should you need them on the exam. This is all explained in the exam email.

I booked my exam for a Saturday evening starting at 5pm.  The email comes right at 5pm. I connect to the network, look at the exam guide that is provided and start working. In the first hour I had managed to root 2 servers. I felt like I was on a roll, and that I was going to end this beast early. Not so much.

After the first two, I didn’t get anything on the next three servers for the next 12 hours. Nothing. Zilch, Nada! I was deflated and dumbfounded. I figured I should take a nap and come back to it. Maybe I am just exhausted and needed some rest. I take a 3 hour nap and come back. This is what I needed. In the next hour or two after that, I had 2 more limited shells. I couldn’t escalate. I tried until the bitter end. At the end, I had two fully compromised hosts, and 2 limited shells. Would this be enough to pass the exam?

Turns out it wasn’t. I got the email Tuesday afternoon stating I hadn’t passed.

I will NOT be defeated!

The Exam (part 2):
I decided to extend my lab time for another 15 days, and book the exam 2 weeks after I had failed. I decided to concentrate on privilege escalations since this is what I was felt I was weak at. I spent the next couple of weeks working on that as well as buffer overflows. I really didn’t too much in the labs, except maybe a few servers I may have missed in the public network. I just really wanted to work on escalations. Turns out this was a smart move on my part.

This time I book the exam for 10AM. Again the email comes, along with the exam guide and instructions to connect in. Away I go. Again, I get the first 2 servers in the first hour. I don’t get a head of myself and just keep plugging away. I start on the next server and it falls in the next hour. By the 5th hour I had 3 full compromises and 3 limited shells. I KNOW I have passed at this point, by the amount of points I will be awarded based on the exam guide. Again… this is not enough for me. I have to prove to myself that I can TRY HARDER!

I do just that.

After 6 hours in the exam, I feel like I am done. 4 full compromises out of 5, and the last server I had a limited shell. This should have been about 90 points. I am satisfied but tired. I was smart enough to document everything as I went, so I only had to spend another hour fixing up my report. I sent my report to the offsec team, and walked away from my computer like a boss.

OSCP Passed!


Wrap up:
This is by far the most challenging and rewarding course and certification I have ever taken. I respect anyone else who has the guts to take this on and succeed. It truly shows you know your stuff in this field.

I sent off my report Saturday evening around 4-5PM. I got the response this morning (Monday Feb 23, 2015) that I had passed the exam. I am elated that this challenge is over and I was able to overcome it. I tried harder when it mattered most and I was able to accomplish what I set out to do.

I am now an Offensive Security Certified Professional because I tried harder!

My OSCP Review

I can not say enough good things about the OSCP course and exam. I was challenged and I learned a whole lot more than I thought I would about security and penetration testing. I hope that the OSCP will gain more recognition by companies. The OSCP is the certification I am most proud of by far.

Time to update the old resume to reflect the new OSCP certification!


Some resources I used for this challenge:

I also read the hackers playbook, the Metasploit unleashed book, and the Penetration Testing book by Georgia Weidman.

These are all very good resources.

Thanks to all those who helped me and pushed me when I needed it, especially all the other people who have written an OSCP review to help others.

More information about the OSCP and PWK can be found here:

Additionally the offsec admins can be contacted via IRC at #offsec

If anyone feels wants to talk or has any questions, feel free to connect to #oscp
I will not give any hints or answers, but I can try and answer any other questions pertaining to the OSCP. Good luck to anyone wishing to take on the OSCP course and exam. After you pass the exam, write your own OSCP review!

OSCP Challenge

I have decided to take on the OSCP (Offensive Security Certified Professional) course and exam.

I decided to tackle the OSCP exam, and make a project out of it.
This thread will be used to document my experiences with the course leading up to the exam.

Course information:
Penetration Testing with Kali

Penetration Testing with Kali Linux (PWK) is an online training course designed for network administrators and security professionals who need to acquaint themselves with the world of offensive information security. This penetration testing training introduces the latest hacking tools and techniques in the field and includes remote virtual penetration testing labs for practicing the course materials. Penetration Testing with Kali Linux attempts to simulate a full penetration test, from start to finish, by injecting the student into a rich, diverse, and vulnerable network environment.

Penetration Testing with Kali Linux is an entry-level course but still requires students to have certain knowledge prior to attending the class. A solid understanding of TCP/IP, networking, and reasonable Linux skills are required. This course is not for the faint of heart; it requires practice, testing, and the ability to want to learn in a manner that will grow your career in the information security field and defeat any learning plateau. Offensive Security challenges you to rise above the rest, dive into the fine arts of advanced penetration testing, and to Try Harder™.

Certification information:

The Offensive Security Certified Professional (OSCP) is the world’s first completely hands on offensive information security certification. The OSCP challenges the students to prove they have a clear practical understanding of the penetration testing process and lifecycle through an arduous twenty four (24) hour certification exam.

The OSCP exam consists of a dedicated vulnerable network, which is designed to be compromised within a 24-hour time period. The exam is entirely hands-on and is completed with the examinee submitting an in-depth penetration test report of the OSCP examination network and PWK labs. The coveted OSCP certification is awarded to students who successfully gain administrative access to systems on the vulnerable network.

Completing this course will allow me to validate my knowledge, as well as learn a lot more. This will be one of the toughest courses I have ever taken.

I am positive that I can complete this challenge and concur the exam.

I will do my best to update this fairly regularly to document my experiences and challenges while going through the course and the exam.