So you failed your OSCP?

If your reading this, chances are that you just failed, or maybe your terrified by the possibility that you might. This post stems from my experiences in failing the OSCP challenge twice, so as Deckard Cain would say, “Stay a while and listen”.


This isn’t a motivational post. I’m not big into motivational material simply because I think it detracts from the reality of what needs to be done in favour of temporarily feeling good. I prefer to frame things in the context of how the actually are.

At any given stage of your development, you’ll have people that has achieved the things you want to and you look up to them. Likewise, there will be others that you can inspire in turn. We’re standing on the shoulders of giants. You know what’s the simple difference between you and them? They have done things that you haven’t. Don’t get me wrong, I know you worked hard (otherwise you wouldn’t be reading this). In fact, forget about the ‘why’ of failing for a second. If you talk to enough of those successful people, you will discover that they all share a handful of traits and experiences. The common denominator that I’m referring to is failure. Every single successful person that I have met, has failed along the way. Most certainly when they least expected it, probably when they least deserved it, and most definitely more than once. Failure is part of the process! It’s so imbedded that it’s almost a prerequisite to success. You failed? Good! Now that it’s out of the way you can tick the box and go on to succeeding.

They have what you want because they were willing to fail, dust themselves off and go on to kick butt. Being willing to fail is just as important as being willing to succeed. Does any of this makes the process of failing suck less? I doubt it, but you know what feels so much worse? Quitting. Your failure would be meaningless if you didn’t put steps in place to succeed the next time.

So the first thing I would suggest, is that you first take a breather. Take a walk, hell even take a few days if you have to until you’re back in your normal frame of mind. When you’re ready, it’s time to come back and examine what happened. You need to figure out what the areas were that you fell short in, and once you’ve done that, come up with a plan to turn them into your strengths.


People often unconsciously spend time practising the things that they are good at and neglecting the things they are bad at because it feels good to get things right and feels bad when your struggling. You know Windows Privilege Escalation like the back of your hand? Good, now leave that alone. Couldn’t find a vector? Work on your enumeration etc. Here are a few questions that you can use to prompt some ideas:

  • Look at the output of a script, program etc, and ask “What about this do I not fully understand?” or “How can I execute code on this machine?”
  • How well did you manage your time?
  • Did you rotate between machines often to avoid getting tunnel vision? If not, then why did you not trust your process of rotating?
  • What were the things that you told yourself when you were not making progress? Was the mental-chatter helpful or harmful?

The aim of this is not to criticise or to beat yourself up (you can’t change what you did), but rather to come up with a plan on how you’re doing to act in the future.

Once you have identified your areas of improvement, you have to commit to yourself that you’re going to follow through on your plan. Book that exam as soon as possible so that you have a time line that your committed to. Plan and plan well, but don’t neglect to take action. If you want to have what you never had, you need to do what you have never done.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s