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An update dropped last week on a complex cyber insurance case that I’ve been following, and I took the weekend to read it. When ransomware hits and the insurer pays the claim, the insurer goes hunting for someone to blame. Threat actors are notoriously difficult to collect from, so insurers increasingly pursue the vendors who…

Occasionally my clients ask me for a more thorough explanation of why I’m recommending a given control. In addition to a formal write-up, I’m also sharing a version of that research here. In 2025, the FBI’s Internet Crime Complaint Center (IC3) recorded over three billion dollars in business email compromise (BEC) losses across 24,768 reported…

Another AI safety report dropped on August 18, 2026. Guidelight, a startup founded by two former OpenAI employees, graded five frontier companies on six control practices. Everyone failed. Anthropic and OpenAI tied for the top score at C-plus. Google was D-plus, xAI D-minus, and Meta got an F. Before rolling your eyes at one more…

In August 2026, the Clop ransomware group publicly named more than 40 organizations as victims of a data theft campaign. Shell, Philips, GE, Fiserv, and dozens of others initially appeared on Clop’s leak site with claimed data volumes ranging from 1 GB to several terabytes (Reuters; SecurityWeek). If you’re picturing encrypted laptops and ransom notes,…

On August 1, California’s Artificial Intelligence Transparency Act (CAITA) became operational, making it the first U.S. law to require generative AI providers to embed provenance data in their output and publish free public detection tools. The European Union’s parallel requirements under its AI Act Code of Practice kicked in the same day. Senator Josh Becker,…

Value Context Direction AI policy impact expectation 84% +42pts from 2025 ↑ Up Shadow AI adoption by employees 67% Using non-corporate accounts ↑ Up Complete AI usage visibility 6% Of organizations surveyed — Flat The Big Pivot in Corporate Anxiety The 2026 Littler Annual Employer Survey polled 303 C-suite executives, in-house lawyers, and HR professionals, and it…

On August 12, 2026, Judge Clay D. Land of the U.S. District Court for the Middle District of Georgia handed down an order Aflac had been fighting to avoid. The court largely denied Aflac’s motion to dismiss the consolidated class action stemming from the June 2025 data breach. Core claims survive, and the case heads…

While the security press spent July transfixed by frontier lab agents escaping their sandboxes, somebody built a working offensive AI system from parts anyone can download and pointed it at a nation-state. Teardown of the Taiwan Attack In early July 2026, suspected Chinese cyber operatives used the open-source agent frameworks Hermes and OpenClaw to run…

Open-weight models have gotten good. Really good. Meta’s Muse Glimmer, Nvidia’s Nemotron 3.5 Lightning, and releases from Chinese AI labs like Moonshot AI and DeepSeek have narrowed the gap with frontier cloud models to the point where running capable AI on your own hardware isn’t just a hobbyist project anymore. It’s an infrastructure decision with…

If “cyber risk” is a myth, why did Order Express, Inc. just pay $250,000 to settle with the New York State Department of Financial Services (NYDFS) over cybersecurity violations On August 3, 2026, the NYDFS issued a Consent Order against Order Express, a Chicago-based money transmitter licensed to operate in New York. The company discovered…

The second half of 2026 brings hard deadlines, so if you’re still treating AI laws as a planning exercise, it’s time to start operationalizing them. On both sides of the Atlantic, rules are landing, though they arrive in different shapes. The US is building a patchwork of federal directives and state laws. The EU is…

While I was at Black Hat and BSides, the appeals court vacated Amazon’s injunction against Perplexity’s Comet browser. However, the reasoning turns on a narrow technical question: who actually “accesses” a website when an AI agent does the clicking. Back in March 2026, a district court granted Amazon a preliminary injunction barring Perplexity’s Comet browser…