Failed OSCP twice — what finally made the difference on my third attempt?

by James R. 51 views3 replies
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James R.OP
May 27, 2026

I've been chasing the offensive security certified professional certification for almost two years now, and I won't sugarcoat it — this exam broke me twice before I finally passed last month. First attempt I ran out of time with only 55 points. Second time I got to 65 but couldn't crack the buffer overflow box and panicked in the final hours. Both times I went in thinking my HTB experience was enough. It wasn't.

What finally clicked for me was slowing way down on methodology. I stopped trying to brute-force every service and started actually reading enumeration output carefully. I also dedicated three full weeks specifically to buffer overflows using structured practice material — including the FREE OSCP Buffer Overflow Questions and Answers on this site, which helped me build muscle memory on the steps. OSCP certification isn't about knowing the most tools; it's about being systematic under pressure.

For anyone else who's failed and is thinking about giving up — don't. The offensive security oscp path is genuinely brutal, but passing it feels different from any other cert. Happy to answer questions about what my 90-day lab approach looked like if that helps anyone.

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Megan P.
May 28, 2026
Can I ask how you structured your 90-day labs? I'm about five weeks into my PWK access and honestly feel like I'm just wandering around popping easy boxes. I haven't touched the Active Directory set yet and I'm nervous about it. Did you do the PDF exercises or skip straight to the lab machines? Trying to figure out how to spend my remaining time.
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Amanda H.
May 28, 2026
This resonates so much. I passed on my second attempt and the buffer overflow section is what saved me — it was the one box I was 100% confident on because I'd drilled it probably 40+ times. The mental shift you described about slowing down on enumeration is real. I used to rush because I was scared of the clock. Once I trusted my process the clock stopped being the enemy.
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Marcus T.
May 28, 2026
Congrats on passing! The offensive security certified professional oscp certification has one of the highest fail rates for a reason. Three attempts shows serious grit. Most people quit after one failure. That persistence is literally what the exam is designed to test.

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