OSCP Week 8: Holiday (2018 Reflection)

Course content: 18/18
Lab machines: 18.5/55
Days: 56/90

So unfortunately, I wasn’t able to meet the target I had placed for myself at the end of last week. I knew it was going to be a stretch goal, as 6 machines in a week was always going to be tough but I do wish I had managed to get even a little bit closer. I still have a few days left before I go on holiday, so will update this post if I manage to make anymore progress before then. Otherwise, there won’t be any actual posts while I’m away. Once I return home I’ll be ready to get straight back into it with more progress updates so make sure to keep a look out for those early next year.

Weekly High:

I feel as though I learned a lot this week, with each machine containing something I had never seen before. Although this meant I was slowed down and therefore wasn’t able to meet the 20 machine goal I was initially aiming for, I’m satisfied with what I was able to accomplish. Because I eased myself into this course by completing the easiest machines first, the labs I am now targeting are noticeably more complex. In some cases, multiple small vulnerabilities need to be used together before I’m able to gain any significant foothold in a machine. This has been draining but very fun, as these small wins stack up to an even greater sense of satisfaction once root privilege has been attained. In particular, my enumeration process got a lot better as I had to use a variety of techniques to learn about obscure services running on a machine. One example was exploiting a directory traversal vulnerability in an open FTP server to fully enumerate a lab machine which lead exploiting another vulnerability to obtain a reverse shell. To do this, I had to teach myself about FTP commands and correct Windows syntax before I was able to get the information required to exploit the machine. It’s this “learn as you go” method that the course uses which I find to be personally very effective, but also very challenging.

Weekly Low:

The “.5” that is added to the tally of my lab machines has given me the biggest headache to date. I decided to include this machine to the total as I was able to obtain a low privilege shell, but have been unable to successfully escalate to root privileges. This has been particularly frustrating because the path to get to the low privilege shell was interesting, and I learned a lot about various techniques such as port knocking, custom word-lists and general web application enumeration. I feel as though I made it 90% of the way there, but have been unable to complete the final step.
Now that I have achieved root on a significant number of machines, I’ve come to realize that privilege escalation is by far my weakest area. Part of this comes down to my relative lack of experience with Linux and Windows system administration, so I’ve had to learn about concepts such as permissions, services, kernels, cron jobs and sticky bits on the go and my knowledge is patchy at best. This has admittedly been tough for me, and I plan to do a bit of reading on privilege escalation while I am on holiday (but only when I can find the time).

I’ll be going on holiday from the middle of next week, which marks my personal end of the year. Reflecting back, 2018 has been one of my busiest, but most fulfilling years. I graduated University and moved cities to start a new job in January, which was a big change in my life and required more adjustment than I had initially anticipated. While at work, I’ve developed both my technical and soft skills with the time I’ve spent in the IT Security team the most valuable in particular. I’ve also been working hard in my own time outside of work to keep learning and improving as much as I can. I passed the Security+ exam in June and have made huge improvements as I make my way toward the OSCP certification, which I am aiming to complete sometime early next year. On top of that, I’ve dedicated time and effort this year into working out at the gym and eating a more balanced diet. It’s been tough at times to stay committed but I have managed to make some significant improvements in my physical health which I am very pleased with, possibly more than anything else I’ve done this year.

In saying all that, I need a break. I have felt myself burning out over these last couple of weeks and have had to keep pushing myself to work hard knowing that I had a holiday coming up where I could unwind. I’m really looking forward to spending time with friends and family and recharging my batteries for next year. I need it!

Have a merry Christmas and a happy New Year,


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