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Compliance Into the Weeds

Compliance into the Weeds: Mapping and Managing AI Agents’ Compliance Risk

The award winning, Compliance into the Weeds is the only weekly podcast which takes a deep dive into a compliance related topic, literally going into the weeds to more fully explore a subject. Looking for some hard-hitting insights on compliance? Look no further than Compliance into the Weeds! In this special episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss a report by Darrow AI on  whether leading LLMs can build privacy-sensitive websites while recognizing compliance obligations.

Darrow had seven “frontier” models build three hypothetical sites involving personal data (pediatric lab results, credit scores, mental health services) and scored them against a privacy/compliance checklist. With no compliance prompting, models averaged about 28/100; with generic privacy prompts, about 63.5; and with extensive documentation and technical specifications, about 88.6 (top model around 95), with none reaching 100. They highlight “ghost controls,” where front-end compliance features (e.g., opt-out buttons) lack back-end functionality. The conversation stresses that prompting quality, technical specifications, and clear human oversight are essential, especially amid layoffs and “vibe coding,” and warns that GDPR/CCPA risks scale with AI speed. They note insurers requested the research and may push governance requirements.

Key Highlights

  • Darrow Study Setup
  • Workplace Oversight Risks
  • Ghost Controls Explained
  • Governance at Scale
  • Beyond Websites to Projects
  • Insurance Pressure Coming

 

Resources

Radical Compliance

 

Tom

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A multi-award winning podcast, Compliance into the Weeds was most recently honored as one of a Top 25 Regulatory Compliance Podcast and a Top 10 Business Law Podcast, and a Top 12 Risk Management Podcast. Compliance into the Weeds has been conferred a Davey, Communicator and w3 Award, all for podcast excellence.