The blog that got me into security: Security Monkey's case files

Tue, 08 Sep 2026 00:00:00 +1300

Before I had a job in security, before I had any of the letters after my name, I had a bookmark. It pointed at a blog on it.toolbox.com written by someone who went by Security Monkey, and it was the best thing on the internet as far as teenage-me was concerned.

The format was simple. An investigator would get pulled into some form of intrigue at one of his clients, a copied CD, a mysteriously missing record, a spike in traffic that shouldn’t be there, and then walk you through the whole thing over a run of numbered parts. “Case of the Arrogant eBayer.” “Case of the Heartless Husband.” “Case of the Mischievous Minotaur,” which ran to twenty-one parts and had me refreshing the page waiting for the next one. They read like detective stories, except the detective work was packet captures, log files and the occasional bit of social engineering. I learned what a lot of this job actually feels like from those posts, years before I did any of it for real.

Then, as these things go, the site went away. it.toolbox.com changed hands, got folded into other things, and eventually the case files stopped resolving. For a while I assumed they were just gone.

They aren’t, entirely. The Internet Archive kept a copy. I can’t overstate how much quiet good the Archive does by hanging on to the web’s dead corners. If you have a few dollars spare, donate to them. They saved something I care about.

Where to find them

I’ve mirrored the case files here, in their own corner of the site so nobody mistakes them for my own writing:

→ The Security Monkey case files

They’re numbered in the same order as Security Monkey’s own official case file index, from the Arrogant eBayer through to the last of them. Start at number one and read forward, or just pick a title that sounds fun. They hold up.

Why I’m hosting them

Partly selfish: I wanted them somewhere I trust they’ll stay. Mostly, though, I’m hoping they do for someone else what they did for me. If you’re a student, a helpdesk person eyeing a move into security, or just curious what the day-to-day of chasing an incident is like, this is a gentle, genuinely fun way in. No prerequisites, no jargon wall. Just a monkey, a keyboard, and a trail to follow.

Credit and a request

None of this is mine. The stories, the characters, the voice, all of it is Security Monkey’s work, and the copyright is theirs. I’m hosting a mirror out of admiration, with full attribution, and thanks to the Internet Archive for keeping the originals alive.

If you’re the author, or you hold the rights, and you’d rather these weren’t here, just email me at blog@thisinsecureworld.com and I’ll take them down. This is a fan preserving something they loved, nothing more.

Community on This Insecure World

The blog that got me into security: Security Monkey's case files

Where to find them

Why I’m hosting them

Credit and a request