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.

Find Scaling Laws on the Lawfare website, and subscribe to never miss an episode.

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This week, Scott sat down with his Lawfare colleagues Benjamin Wittes, Daniel Byman, and Ari Tabatabai for an in-depth discussion of the U.S. military operations against Iran, including:

• “Isn’t it Iran-ic.” Trump’s decision to join Israel in removing Ayatollah Khamanei reflects a deep reversal by the president, who has spent years criticizing his predecessors’ own experiences with regime change and other overseas adventurism. What drove Trump to proceed this time, after stopping short twice in the past year? What can we learn from the way the Trump administration has proceeded? And how far will Trump let things go?
• “Bibi’s Big Adventure.” Regime change in Iran is something Israel and the Arab Gulf states have advocated for frequently in the past. But they had all adopted a more cautious and even conciliatory posture toward Iran in the months before the current offensive, at least in public. How has the region approached this conflict? And what will it do moving forward?
• “MIGA.” The death of Ayatollah Khamenei is a major shift in Iran, but we don’t know where it is going to lead. One concern that people have always had about regime change in Iran is that it will be highly destabilizing, resulting in a failed state in a crucial corner of the Middle East. On the other end, other people have asserted that removing the Ayatollah and his regime will give Iran the opportunity to flourish back into a democracy, or at least something closer to a state that’s more stable and free than Iran has been for the last several decades. Between the two is a mass spectrum of possibilities. What does the future hold for Iran in the post-Ayatollah era, if that’s the era that we’re heading into?

In object lessons, Ben is vibe-coding his way through Lawfare’s litigation tracker, as well as vibing his way through The Rest is History’s four-part series, Revolution in Iran. Dan is war-gaming his way through the attack on Iran with Next War: Iran. Scott is consuming as much Iran content as he can get his hands on with (another) Scott Anderson’s “King of Kings,” Roy Mottahedeh’s “The Mantle of the Prophet,” Gary Sick’s “All Fall Down,” and Dutch documentary “The Birthday,” finally discovered online by Lawfare’s own Anna Hickey. And Ari, not to be outdone in Iran content, recommends the graphic novel “Persepolis,” but really is escaping it all with Final Fantasy VII Remake.

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For today’s episode, Lawfare Senior Editor Scott R. Anderson sits down with three leading scholars from the Georgetown University Law Center—Professor Kathleen Claussen, Professor Marty Lederman, and Visiting Scholar Peter Harrell of the Institute of International Economic Law—to talk through the Supreme Court’s groundbreaking opinion in Learning Resources, Inc v. Trump, which invalidated the array of global tariffs that the Trump administration had imposed using the International Emergency Economic Powers Act (IEEPA).

Together, Scott and his guests break down the Court’s opinion, weigh what it might mean for the Major Questions Doctrine and foreign relations law, and look ahead to the legal fights to come over the other tariff authorities the Trump administration is now using to pursue its agenda.

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In a live conversation on March 2, Lawfare Editor in Chief Benjamin Wittes spoke to Lawfare Senior Editor and Research Director Alan Rozenshtein about the Pentagon's designation of AI company Anthropic as a supply chain risk, the implications of a designation, how other AI companies have reacted, and the legal challenges the designation may face.

Read Rozenshtein’s article on the topic, co-authored with Michael Endrias, here.

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In a live conversation on YouTube, Lawfare Editor in Chief Benjamin Wittes sat down with Lawfare Senior Editors Scott R. Anderson, Roger Parloff, Molly Roberts, Anna Bower, and Alan Rozenshtein, and Lawfare Public Service Fellow Troy Edwards to discuss the superseding indictment in the case against Don Lemon and his co-defendants in Minnesota, the standoff between the Department of Defense and Anthropic, the firing of FBI agents who worked on the classified documents case, and more.

You can find information on legal challenges to Trump administration actions here. And check out Lawfare’s new homepage on the litigation, new Bluesky account, and new WITOAD merch.

To receive ad-free podcasts, become a Lawfare Material Supporter at www.patreon.com/lawfare. You can also support Lawfare by making a one-time donation at https://givebutter.com/lawfare-institute.

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From February 27, 2025: For today’s episode, Lawfare Senior Editor Scott R. Anderson sat down with Kathleen Claussen, an expert in international economic law and professor at the Georgetown University Law Center, and Lawfare Contributing Editor Peter Harrell, a non-resident senior fellow at the Carnegie Endowment for International Peace, to discuss the ambitious set of tariffs the Trump administration has imposed or threatened over its first month in office.

They discussed the tariffs Trump has imposed so far, what seems to be coming over the horizon, and how they all line up with the legal authorities he is using to impose them.

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