Chief Monkey’s Case Files

UPDATE: I was able to get in touch which the original author, and he has decided to relaunch his blog on the Medium platform. I have hidden all of the previous case files and will be linking to them on his Medium page (https://medium.com/@chiefsecuritymonkey) as he re-peels those bananas.

Several years ago when I was just discovering my interest in information security, I stumbled across a series of blog posts on it.toolbox.com written by someone going by the name of Chief Monkey. In these posts, he described different cases he has worked on during his time as an independent Information Security Investigator with names and identifiable information changed in order to abide by non disclosure agreements. The stories written there were something that I personally found motivating, inspirational, and most importantly entertaining.

While I had already begun discovering my interest in information security, reading about the Chief’s antics showed me a way to apply this interest to an exciting career which is something I had not really known at that point in my life. I found myself coming back to his case files time and time again, sometimes to break myself out of a rut and find that motivation again, and sometimes for no other reason than his excellent story telling. I shared this blog with every friend of mine that would listen, and then one day in late 2019 the blog was taken offline.

After an appropriate period of grieving for my loss of what amounts to a personal hero that I’ve never met, I found a mostly-complete archive of the blog posts on web.archive.org’s Wayback Machine, so I decided to take this opportunity to preserve what I could of these holy texts here on my blog. I am not the author of any of these, but I wanted to ensure that they were readily available to inspire the next generation of professionals that may never otherwise know a career like this is a possibility.

You can find Chief Monkey on Twitter at @chiefmonkey. Chief, if you ever see this, thank you for sharing these stories. I’m not there yet, but I hope to develop my career into a something similarly entertaining and helpful.

Case of the Arrogant Ebayer

Part I
Part II

Case of the Talkative Terrorist

Part I
Part II

Mysteriously Missing Records

Part I
Part II

Case of the Careless Whisper

Part I
Part II
Part III
Part IV
Part V
Conclusion

Case of the CFO CD

Part I
Part II
Conclusion

Case of the Drive-By-Spammer

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Part XII

Case of the Heartless Husband

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Conclusion

Case of the Hushed Hax0r

Part I
Part II
Part III
Part IV
Part V
Part VI

When things go bad

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII- It ends badly

Case of the Determined Debutant

Part I
Part II
Part III
Part IV
Part V – Missing
Part VI
Part VII
Part VIII

Case of the Agitated Ad Peddler

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Part XII
Part XIII
Part XIV
Conclusion

Case of the Bandwidth Burglar

Part I
Part II
Part III
Part IV
Part V

Case of the Prying Eyes

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X – Missing
Part XI
Part XII
Part XIII

Case of the Stealthy Spike

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Part XII
Part XIII

Case of the Mischievous Minotaur

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Part XII
Part XIII
Part XIV
Part XV
Part XVI
Part XVII
Part XVIII
Part XIX – Missing
Part XX
Part XXI

Case of the Audacious Attacker

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Part XII
Part XIII
Part XIV
Part XV
Part XVI
Part XVII
Part XVIII
Conclusion

Case of the Tepid Tipster

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Part XII
Conclusion

Case of the Leaky Leaf

Part I
Part II
Discussion of Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Part XII
Part XIII
Conclusion

Guest Blog: Case of the Lascivious Lawyer

Part I
Part II
Conclusion

Case of the Lucrative Lure

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Part XII
Part XIII
Conclusion

Case of the Teetering Timeframe

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Conclusion

Case of the Heaping Haystack

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Conclusion
Redux

Case of the Ethical Executive

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
The Conclusion

Case Of The Innocent Iris

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Conclusion

Case Of The Robotic Reflex

Part I
Part II
Part III
Part IV
Part V
Part VI
Part VII
Part VIII
Part IX
Part X
Part XI
Conclusion

Case Of The Tenacious Timelord

Part I
Part II
Part III
Part IV
Part V
Part VI