Alan Rozenshtein, research director at Lawfare, spoke with Cullen O'Keefe, research director at the Institute for Law & AI, and Kevin Frazier, AI Innovation and Law Fellow at the University of Texas at Austin School of Law and senior editor at Lawfare, about their paper, "Automated Compliance and the Regulation of AI" (and associated Lawfare article), which argues that AI systems can automate many regulatory compliance tasks, loosening the trade-off between safety and innovation in AI policy.

The conversation covered the disproportionate burden of compliance costs on startups versus large firms; the limitations of compute thresholds as a proxy for targeting AI regulation; how AI can automate tasks like transparency reporting, model evaluations, and incident disclosure; the Goodhart's Law objection to automated compliance; the paper's proposal for "automatability triggers" that condition regulation on the availability of cheap compliance tools; analogies to sunrise clauses in other areas of law; incentive problems in developing compliance-automating AI; the speculative future of automated compliance meeting automated governance; and how co-authoring the paper shifted each author's views on the AI regulation debate.

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Alan Rozenshtein, research director at Lawfare, and Kevin Frazier, senior editor at Lawfare, spoke with Amanda Askell, head of personality alignment at Anthropic, about Claude's Constitution: a 20,000-word document that describes the values, character, and ethical framework of Anthropic's flagship AI model and plays a direct role in its training.

The conversation covered how the constitution is used during supervised learning and reinforcement learning to shape Claude's behavior; analogies to constitutional law, including fidelity to text, the potential for a body of "case law," and the principal hierarchy of Anthropic, operators, and users; the decision to ground the constitution in virtue ethics and practical judgment rather than rigid rules; the document's treatment of Claude's potential moral patienthood and the question of AI personhood; whether the constitution's values are too Western and culturally specific; the tension between Anthropic's commercial incentives and its stated mission; and whether the constitutional approach can generalize to specialized domains like cybersecurity and military applications.

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Kevin Frazier sits down with Andrew Freedman of Fathom and Gillian Hadfield, AI governance scholar, at the Ashby Workshops to examine innovative models for AI regulation.

They discuss:

• Why traditional regulation struggles with rapid AI innovation.
• The concept of Regulatory Markets and how it aligns with the unique governance challenges posed by AI.
• Critiques of hybrid governance: concerns about a “race to the bottom,” the limits of soft law on catastrophic risks, and how liability frameworks interact with governance.
• What success looks like for Ashby Workshops and the future of adaptive AI policy design.
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Whether you’re a policy wonk, technologist, or governance skeptic, this episode bridges ideas and practice in a time of rapid technological change.

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