Tips on preparing and passing your OSCP+ exam from a Security Analyst (x) who passed on their first attempt!

OSCP

Back in September 2025, I sat and successfully passed my OSCP+ exam on my first attempt! I got my 70 points for a passing grade in a little over 5 hours, completing the AD set in under a hour as well!

As someone with only ‘Defensive’ security experience, but who really enjoys CTF/HTB challenges I wanted to take the OSCP exam to undertake what was a fun and exciting challenge (Also a bit shamefully for the clout lol).

Enough with the bragging though, when prepping for the exam I found reading about others experiences really helpful, so I wanted to offer my own perspective and advice in the hope it can help someone else undertaking there exam.

Preperation Tips

Tips in the lead up to the exam

Practice!

This covers my recommened approach to ‘practice’ AND how to identify when your ready for the exam!

Practicing may seem obvious, but I think a key tip from me would be to not just practice, but get good practice!

I think it’s important when preparing for the OSCP to focus on machines with content/a style that will be similar to those seen in the exam. What’s also key and incredibly key though is to not rely to heavily on write-ups (or even small hints) when preparing for the OSCP!

During the exam you won’t be able to get any external assistance at all (e.g. through a write-up or hint), so it’s incredibly important you feel comfortable doing boxes/sets without any assistance.

For me write-up/no write-up is a totally different game. With a write-up/hint you’ll always have some idea of where to go next, but without these you need to be comfortable being uncomfortable and working through your enumeration in order to know where to go next.

That being said, towards the start of your learning absolutely use write-ups, especially for harder/more challenging machines! Write-ups provide great insight into what others do and you can always learn from this to improve your own style, you just need to be sure you don’t make them too much of a crutch, especially when it comes to exam time.

Every time you do use a hint just ask yourself why you needed to use it after finding where you went wrong/what you missed. Don’t just take the hint and run, but try and reflect on what was missing that prevented you from getting there on your own, this really helped me!

When it comes time to book your exam, considfer this exercise for identifying if your ready. Choose 5 (Proving Grounds) machines at random from the Tj Null/NetSecFocus Room list (https://docs.google.com/spreadsheets/u/1/d/1dwSMIAPIam0PuRBkCiDI88pU3yzrqqHkDtBngUHNCw8/htmlview ). Try doing these machines with no assistance at all and see how you go! Don’t be discouraged if you can’t do them all without write-ups, but I’d aim to be able to at least bee able to do 4/5 without any help before heading into your exam. But don’t let this discourage you either! Not all machines are equal and honestly a big part of the exam is down to luck of what your going to get for those standalones!

Develop Strong ‘Checklists’ for your enumeration, but DON’T Re-Invent The Wheel!

Having a checklist of what you should be checking during your enumeration phase will be a massive help during the exam.

While doing your practice boxes in the lead-up to the exam, take note of useful commands for enumeration and what your checking. You can use this information to make a checklist and during the exam it can come in as a massive help!

The exam can be very stressful and you don’t want to be relying on memory alone of what you should be doing, so a checklist can be very useful.

Do note, you don’t need to re-invent the wheel here either though! So many guides to enumeration different services are available online and you’ll likely encounter at least some service during the exam you haven’t seen before. So when/if you do, simply google ‘x service enumeration pentesting’ or something similar and chances are you’ll find someone else’s steps you can use!

Tips for the Exam

Take HIGH QUALITY Breaks

A mental reset can be key during the exam.

If you find yourself stuck for an extended period of time, a decent break to reset your brain may be what you need.

For me, a decent break is one where I’m able to go do something else that takes my focus away from the core task, which then when returning to the core task gives me a bit of a reset.

Of course for OSCP your time is going to be limited so you can’t take a massive breaks to reset yourself, but absolutely try and get up for a walk, make a tea or coffee (and drink it away from your PC to try and reset!) or do something that works for you!

Don’t overlook anything as part of your enumeration/initial access

Key tip for the exam

During the exam you’ll of course be faced with several boxes you need to root.

Without giving anything away, you’ll obviously be charged with enumerating different services on each of these boxes.

Now a trap I fell for was seeing services and before even looking thinking (1) oh it’ll likely be this OR (2) oh they wouldn’t make it X that’d be too easy!

Now for me this was a massive trap! Don’t overlook anything as part of your enumeration/initial access phase and try everything you can!

TIP: Don’t get stuck in the loop of running the exact same commands and expecting a different outcome. You’re probably in a rabbit hole if your at this stage!

Try and Chill Out!

Listen to music and try not too stress to hard!

For me at least, being overly stressed/nervous really gets in the way of my thinking. I know for such a big investment like OSCP it can be hard to try and set aside stress, but getting in a more chill mindset can be a absolute godsend for the exam and put your best foot forward.

Great Learning Resources!

Resources I highly rate for preparing for the exam.

TryHackMe and/or HackTheBox https://tryhackme.com/ https://app.hackthebox.com/

Both of these sites are great at supplying boxes for learning/practicing new techniques.

The debate between the two sites will always be a thing, but while I prefer HackTheBox now days if your earlier on in your journey I would rate TryHackMe as it’s got some awesome learning pathways that can be far less dauting for beginners. HackTheBox in my opinion though provides a lot more challenging/fresher content, so it’s great once you have more experience (but can be hard for beginners cause I swear some of those easy boxes don’t be EASY!!!)

NetSec Trophy Room https://docs.google.com/spreadsheets/u/1/d/1dwSMIAPIam0PuRBkCiDI88pU3yzrqqHkDtBngUHNCw8/htmlview

The most useful resource I found for my exam was this list of boxes. This is a list of ‘OSCP like machines’ curated by Tj Null and has machines that are ‘similar’ to those you’ll likely encounter during the OSCP exam.

I’m a very practical learner, so having a list of machines to focus on doing was awesome for preparing for the exam.

I’d highly recommend focusing on these machines when preparing for your exam and really try and get use to doing them without write-ups or hints once you have experience!

OffSec https://www.offsec.com/

This may seem incredibly obvious, but while the learning content for the OSCP+ does draw mixed reviews it’s still important to acknowledge the exam is being supplied by OffSec so I think it’s very important to focus on the machines/learning content from Offensive Security!

In my opinion, the boxes both directly listed under the OSCP+ learning content (Supplied as part of the course) AND the boxes you can find on OffSec’s Proving Grounds content are the most usesful/similar to those you’ll see in the exam, so I’d focus on these while learning! (Don’t forget to use the TJ Null/NetSec Trophy Room list of OffSec/Proving Grounds machines!)