2020 OSCP Contest

Last year I decided to give away 3 vouchers to PWK 60 days of labs. This was of my own free will and under no umbrella. I wanted to give back to the community and industry that provided a means to which I can feed, clothe, and put a roof over my family’s head.

But, how to give away something like this? I didn’t want it to go to people who just were faster at coding than someone else, or could figure out some obscure CTF challenge. I wanted it to go to someone that was hungry to learn and hungry to achieve more, so I devised a 3 stage challenge.

Here is the original post about it:

Challenge 1:

Get two people to send us a letter of recommendation. This didn’t have to be formal and could very easily just be a direct message from them. We used this challenge to get a sense for your effect on others. Someone who does good for others has no trouble finding people who will speak well of them. This was also a test to see if you had the perseverance to ensure both people contacted us.

Challenge 2:

Send us information about a topic in Infosec you are passionate about and write a little bit about it. This could just be the word “Forensics”, but the caveat is that you needed to convince us of why you are interested in that topic and show passion for it. No limit or requirement of length, but one word answers will probably not make it to the next round.

Challenge 3:

The final challenge would be based on your answer to challenge 2. We asked participants to write up a topic pertaining to their passion or selected interest. This will need to be at least a couple paragraphs.

Thats it. If you made it through to the final challenge by showing enough effort, We put in the effort to read every entry and selected the ‘best’ top 3 based on the participants:

  1. Respect (of time, mine, theirs, and others)
  2. Perseverance
  3. Humility (not self-deprecation)
  4. Resourcefulness (specifically in challenge 3, to learn something new)

This year. We are doing it again. This time, I have more help. Along with SpikyGeek, the amazing Int0x80 from @dualcoremusic will be joining me on helping to judge the contest, and this year, there are FIVE (5) vouchers graciously donated from the Offensive Security team. So there will be a TOP 5.


  1. ALL submissions must be done via direct message to the OSCPGiveaway twitter account. This means that if you want to submit a PDF or doc or whatever, you need to post a link to a Google Drive file or some other means. Emails regarding the contest to any of the contest committee will be ignored.
  2. All announcements will go through the twitter account as well, so you should turn on notifications for that account if you want to keep up to date with things.
  3. If you have more than 2 letters of recommendation sent to us, we will assume you don’t respect my time and disqualify you due to the tenets of the contest. We do not have all the time in the world and there are only three of us looking through every person’s submissions in this contest. We don’t have infinite time to do so.
  4. If you cannot seem to follow the directions as they are laid out in the above document, you will be disqualified. Read carefully.
  5. In your first DM to the twitter account include your favorite emojii by itself just to show that you actually read these rules. This will be how you enter the contest.
  6. Random mentions sent to us or the team on Twitter are not Direct Messages, people vouching for you, or endorsements this way will be ignored and not count towards your contest submissions.

Addendums and Clarifications

  1. Challenge 3 is supposed to be a question/topic that we (the organizers) chose based on the topic you submitted for Challenge 2. Apologies for the confusion here. It will be worded better next year.
  2. You do not have to wait for any acknowledgment to submit Challenge 1 and Challenge 2.


Challenge 1: December 5th

Challenge 2: December 10th

Challenge 3: December 26th

Winners Announced on January 2nd 2021