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Weekly News Context June 12
Here's everything important that happened in the cybers this week.

In addition to regular commentary, I'll be releasing free resources from my book, Cyber Risk is a Myth. These resources come with written and video explanations, and templates in multiple formats. And to make it interesting, I'm releasing them in random order.

When the Algorithm Cancels Your Coverage Before You Know It

Car insurance concept
Key quote: Consumers deserve transparency and fairness throughout the insurance process, especially when losing coverage can leave someone unknowingly uninsured and vulnerable to penalties and financial risk. Why it matters: Since 2021, the insurance sector has chased AI efficiency gains only to get stuck in a cycle of lawsuits and settlements. The latest example is from Pennsylvania, where Attorney General …

Blog

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Stop Wasting Money on Reports Nobody Reads - The Business Impact Translation Matrix

Stop Wasting Money on Reports Nobody Reads - The Business Impact Translation Matrix Rather watch this than read this? Neat. Security reports die in inboxes every single day. You write them, send them, and they vanish into the digital void until a breach forces everyone to pay attention. The problem isn't your technical work; it's your language. You speak in …

Resource Library

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What happens when police let an algorithm do the investigating

Close up view of security camera on building in sunlight
Key quote: What looks like a second, independent identification is in fact the same algorithmic error surfacing twice, creating an illusion of confirmation that drives officers to treat the result as reliable. Why it matters: Robert Dillon is a commercial crabber from Fort Myers who'd never been to Jacksonville Beach and was arrested due to a combination of faulty technologies …

Blog

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The Role-Based Risk Awareness Program Template

The Role-Based Risk Awareness Program Template Why read when you can watch this instead? Most security training fails because it treats everyone the same. You send the same phishing video to your chief financial officer and your machine shop floor manager, and they both click the training link, and ignore the content. One month later, they both fail the phishing …

Resource Library

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Cox Media Group Sold Fake Voice Listening Tech

Young handsome freelancer in pajamas working with laptop on couch
Key quote: Voice Data means any full or partial audio file of an individual's voice, voice communications, or audio communications, as well as any transcripts of such audio file. Why it matters: Cox Media Group tried selling clients an AI-powered "Active Listening" service that doesn't exist, claiming they could listen to dinner conversations to serve vacation ads when you talked …

Blog

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Fake It Till You're Indicted

Empty Shopping Cart Casting Shadow on the Wall
Key quote: The requested stay would prejudice no party to this civil action; would prevent the circumvention of important statutory limitations on criminal discovery and avoid asymmetrical discovery; and would preserve the Court's resources because many of the issues presented by the civil action will be resolved in the Criminal Case. Why it matters: The SDNY's asked its civil court …

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11% of CXOs say they're ready for 1,661 AI agents, I'm sure that's fine

IBM 2026 tech leader study redefining the tech leader s mandate report
Key quote: "The most critical architectural capability is integration. We don't know what's coming next, so the foundation must support constant change." Why it matters: Eleven percent. That's the share of 2,000 CXOs who told IBM and Oxford Economics they're fully prepared for the scale of agentic AI deployment expected in the next 12 months, while the other 89% are …

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Words in other places:

Lists I got added to:

And here I thought only the North Koreans had me on a list.

Cases I'm watching:

  • Couture v. Openai Global, LLC, 3:26-cv-03000
  • Conservation Law Foundation, Inc. v. Shell Oil Company, 3:21-cv-00933
  • Amazon.com Services LLC v. Perplexity AI, Inc., 3:25-cv-09514
  • E.P. v. Medvi, LLC, 2:26-cv-03796
Thanks, and have a great weekend! This newsletter is published every Friday I'm in the office.

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