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Nearly 180 days ago I decided to work towards the OSCP. An Offensive Security Certified Professional. I chose to sit this because of what I’ve heard from industry professionals about how much it can teach you with the training materials provided by Offensive Security and that it would land me a job ASAP. These two combined made it a no brainier to take. After buying the exam, I began to try hard TryHackMe, then the summer hit and I spent all my time interning, then I had 8 weeks left to take the exam. I began on the training material provided but didn’t get very far in the 860! PAGE learning material. Then the day before the exam, my exam was scheduled for 7:00 am so I made some prep the night before and nicked the air-firer out of the kitchen and the coffee machine ( Not partner approved ). Already I went to bed a few hours earlier than normal just to make sure the anxiety would pass, but I felt ready for the exam, I thought I had it in the bag, but I was sorely mistaken.

The Attempt

I had planned to spend about 2 and a half hours on the non-AD boxes and then the rest of the time on the AD set. I got somewhere with the second non-AD box but still no flag so I moved on to the AD set. Still nothing. By this point it was 4 pm and as the exam is 24 hours I decided to take a break and have a nap. After my 3 hours of sleep, I got up and back to it. Then success, I gained access to one of the non-AD boxes for 10 points! Yes, I had something but it was all downhill from there I had 10 hours left ALL of which I spend enumerating the machines. Over time tension kept building and I was getting very frustrated. There were so many rabbit holes and I got stuck in all of them. At 6:50 am the next day the proctor told me it was time to finish. I had 10 out of the 70 points needed so it’s a fail. I’ve since figured out exactly why I failed and what to do about it.

Getting better.

  • Not enough sleep – Trying to work for 21 hours with only 3 hours of sleep was a terrible idea. next time I’m going to dedicate at least 6 hours.
  • Not enough food – Over that period of time I only had 3 meals at small portion sizes. That’s not enough energy for a person to work on. Next time I’ll meal prep something proper to eat in good portion sizes.
  • Practice practice practice – I’m going to aim for one box on HackTheBox per week from now on.
  • Not enough breaks – I took 2 breaks over the 24-hour period, one was to sleep the other was to get food out of the fridge. This isn’t enough time to be able to work effectively. Next time I’m going to take a 20-minute break every 3 hours.
  • Rabbit Holes – I need to get much better at enumeration, it’s arguably the most important skill for a red team member and yesterday I learnt how bad I was at it.
  • Play some Mario Kart – I took no time to de-stress or reset myself. I thought purely working hard would be enough. It wasn’t. Next time I’ll use my breaks to play a game or do something fun.

But I’m not done. I’m going to get the OSCP before I finish University. All I need to do is improve.

P.S. After getting set up I had 10 minutes before my exam started so I played tic tac toe with the proctor ( board below ), it ended up taking 20 minutes for my email to arrive so we had a good few games.

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