Road to OSCP: Week 1

Since this is the first writing I’m doing here, it warrants some introduction. My name is Tristan, I’ve just finished my second year of undergrad at Lewis & Clark College in Portland, Oregon. I’m a Computer Science major, and I specialize in Security within CS. 

What I’m doing

Over the next few months, I’m shooting to test for my OSCP. The OSCP is a penetration testing cert, which is famously regarded (at least to the people I’ve talked to about it) as the badge that says “I’m a pentester good enough to be taken somewhat seriously”. It’s a damn hard test, and I’ll have to clock a lot of hours in to making it happen, but I think I can pull it off before classes start back up in the fall. 

Why I’m doing it

I’ll be applying for security internships for next summer starting in the fall, so I was looking at ways to prep for those interviews this summer. So, the OSCP. I was at first thinking of going for an easier pentesting cert, like the EJPT, but I decided to go for the stretch goal. I figure that even if I fail it the first time I take it, I’d rather say that I failed a harder test than have played it safe and done something less impressive. 

What I already know

What I find frustrating about “I did the OSCP, here’s my story” articles and posts is that a lot of them don’t go into details with what experience the test taker already has, so it’s hard to get a good grasp on how hard the exam is. With that in mind, here’s exactly what I know:

Operating systems: My Desktop is a Windows 10 machine, my laptop runs macOS, and my college uses mainly Ubuntu machines for CS classes, so I’ve got good experience with all OSes. My unix command line skills are solidly average. 

Security skills: I’ve done a number of CTF’s, Attended DEFCON twice, and keep up to date on security happenings- all of which has given me a good introduction to a wide variety of security topics. I’m at least familiar with almost all concepts- I can listen along to conversations about security without having to stop and look things up, most of the time. 

Pentesting: Again, I know how to use a small handful of the simplest Kali tools well (nmap, hashcat, dirbuster, and aircrack come to mind), and a passing usability with the rest. I’ve rooted 2 machines on Hack the Box last summer, but they took a really long time and I needed a lot of help. 

Programming: I’m great with Python and C, and just a touch slower with Java. 

As a part of my college’s blue teaming club (It’s an informal group, we have yet to come up with a good name), I have experience with Windows Server administration, specifically with Active Directory. I can to setup and installation of all the services, configure permissions / accounts, and know some of how to secure a windows machine. 

It’s hard to crunch down my entire skillset into a few paragraphs, but I feel that’s sort of the point. I haven’t quite made jack-of-all-trades status; I’m probably at about ~30% familiarity with ~80% of the trades. 

What I did this week

I don’t actually get access to any of the official OSCP material for another 2 weeks, but I’m calling this week 1 because I’ve started working for the thing anyway. This week I’ve been watching a lot of youtube videos on the things I’m already a little familiar with- nmap, netcat, reverse/bind shells, and some of the less obvious uses of Kali- for example, I’d never heard of Nmap NSE scripts, and never really understood the differences between a reverse shell and a bind shell. 

 I’ve also watched a few of Ippsec’s Hack the Box video writeups, Irked and Teacher. These are useful for identifying a tentative workflow of how one goes about enumerating a machine, how to look for vulnerabilities, and getting past the “now what” phase of information gathering. I’m working on another HTB machine, Netmon, on which I’m making good progress. 


This is, as you can see, my first of these blog posts. It’s also the first time I’m writing about my work like this, and the first time I’ve got myself a website, and my first time going for this level of cert- there’s a lot of firsts here, so things may change. However, I’d like to stick with it, and here’s hoping that some readers will too. 

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