The Inside Scoop on Insider Risk - by Omer Singer
Ask an experienced CISO which initiatives have had the least success in making it from plan to production, and you’re likely to hear about Insider Risk or Insider Threat Detection. There are good reasons to invest in stopping disgruntled or dishonest employees from misusing their access… it’s just hard to do. Meanwhile, the allure of machine learning for solving the problem drives organizations down the path to project failure time and again. In this post, I’ll introduce Mencken’s Law of Threat Detection to explain why this keeps happening and how you can swing the odds in your favor. H. L. Mencken was a famously pessimistic American journalist and critic. A hundred years ago, he wrote classic gems like "No one ever went broke underestimating the intelligence of the American public" and "Bachelors know more about women than married men; if they didn’t they’d be married too." His relationship pessimism might be misguided, but it’s right on the money for insider threats. How serious is t
Ask an experienced CISO which initiatives have had the least success in making it from plan to production, and you’re likely to hear about Insider Risk or Insider Threat Detection. There are good reasons to invest in stopping disgruntled or dishonest employees from misusing their access… it’s just hard to do. Meanwhile, the allure of machine learning for solving the problem drives organizations down the path to project failure time and again. In this post, I’ll introduce Mencken’s Law of Threat Detection to explain why this keeps happening and how you can swing the odds in your favor. H. L.…
related reading
- Insider Threat: Hunting and Detecting | Google Cloud Blogcloud.google.com
- How to Detect & Prevent Insider Threats (2026)cyberhaven.com
- Looking Within | Strategies for Detecting and Mitigating Insider Threatssentinelone.com
- The Power of the Marginalpaulgraham.com
- Insider Threats | Exabeamexabeam.com
- A gentle introduction to mechanistic anomaly detection — LessWronglesswrong.com
- secret-loyalties-whitepaper.pdfformationresearch.com
- Security incident disclosure — July 2026huggingface.co
- Agentic Misalignment: How LLMs Could be Insider Threats — LessWronglesswrong.com
- The Power of the Marginalpaulgraham.com
- Focus Threat Intel Capabilities at Detection Engineering (Part 4) | by Anton Chuvakin | Anton on Security | Mediummedium.com
- Ten people on the inside — LessWronglesswrong.com