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Creepy Co-Worker Won't Shut Up About 'Pentests'

News - 2026-07-22

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A person using a computer in a dark room, entering secret info like their password. Someone else is watching from behind. They must like to watch.

Junior developer Harold Harrelson was fascinated to learn the software he maintains had its security audited with something called a 'Pentest'. An assessment run by cybersecurity professionals to test the security of software by attempting to hack into it. Harold is so fascinated, he hasn't stopped talking about it since.

"Did you know pentests are necessary to ensure the software you develop is secure? We should have all of our software penetrated...I mean, pentested," he announced to everyone, unprompted.

People aren't sure if they should report him to HR, or be annoyed. "When he starts talking about pentesting, I walk away. I can't tell if he's so innocent he doesn't know what he's saying, or if he knows how to walk the line just enough to not get reported," said I.T. Admin Peter Peterson.

Carol Carolson, a QA engineer at the company let us know, "Is he even trying with the innuendo, or is it all going over his head? I've heard the same 'penetration' line from him for three weeks. 'A good pentest should use every endpoint,' is right there and he hasn't even realized it!"

Chris Christian in HR told us, "We're not allowed to comment on cases like this. But, yeah, we're going to do something."

Other phrases he has been reported to HR about include, but are not limited to:

When asked if he's planning to skill-up on cybersecurity and penetration testing concepts for a career change, he replied, "No. But I wish they'd let me watch."