Caveat
Join us for thought provoking conversations on surveillance, digital privacy, and cybersecurity law and policy in the information age. Each week, hosts Dave Bittner and Ben Yelin break down the headlines, legal cases, and policy battles that matter most.
Episodes
June 18, 2026 • 45 mins
This week, Dave and Ben take a look at a recent ruling against Google by a German court holding them liable for any false statements generated by its AI Overviews. Additionally, the two examine how Congress failed to extend Section 702.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For official legal advice on any of the topics we cover, please contact your attorney.&...
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June 11, 2026 • 45 mins
This week, Dave and Ben sit down with N2K's lead analyst Ethan Cook to examine President Trump's recent Executive Order centered on AI. With this order, the Trump administration is looking to increase its oversight of new AI models to better account for potential security vulnerabilities before public releases, marking a key development in the administration's AI policy stance.
While this show covers legal topics, and Ben is a la...
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June 4, 2026 • 38 mins
This week, Dave and Ben sit down to Florida's recent lawsuit against OpenAI and Sam Altman. In the suit, Florida alleges that the company placed profits over safety needs. Additionally, the two cover a story on an ad-based surveillance network.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For official legal advice on any of the topics we cover, please contact your at...
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May 28, 2026 • 35 mins
This week, Dave and Ben sit down to discuss a growing bipartisan effort to support CISA. Throughout the conversation, the two look at how lawmakers from both sides of the aisle are showing greater support for CISA after the Trump administration cut its budget and workforce. Both Representatives Don Bacon and James Walkinshaw voiced their support for the agency, emphasizing that it was essential to protecting civilian networks and c...
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May 21, 2026 • 40 mins
This week, Dave and Ben sit down to discuss two legal cases. The first case involves Santa Clara suing Meta over alleged scam ads. The second story looks at a now dismissed case where the lawyers could potentially face consequences for allegedly using fake AI citations in their filings.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For official legal advice on any of ...
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May 14, 2026 • 47 mins
This week, Dave and Ben sit down to discuss how Sony's failed lawsuit could have major impacts on other copyright lawsuits alongside how the EU's AI approach might be grounded in nuclear deterrence strategies. Additionally, our team sits down with Dr. Liz James, a managing security consultant at the NCC Group to discuss the EU's new cybersecurity regulations that were instituted as a part of new vehicle emission regulations.
While...
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May 7, 2026 • 52 mins
This week, Dave and Ben look at how the Trump administration is reshaping federalism through AI policy alongside looking at a lawsuit filed by a college student against a dating app for using her image without permission. Afterwards, Ben sits down with Jen Sovada, Claroty’s Public Sector GM, to discuss national cybersecurity strategies and how these initiatives depend on public-private trust.
While this show covers legal top...
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April 30, 2026 • 43 mins
This week, Dave and Ben sit down with N2K's Lead Analyst Ethan Cook to look at the Supreme Court's new case examining geofencing. In the conversation, the three break down the various stances the justice's have already begun to take up and what the potential fallouts of this case could be.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For official legal advice on any ...
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April 23, 2026 • 42 mins
This week, Dave and Ben revisit several key stories including the Senate reauthorizing Section 702 and top White House officials meeting with Anthropic's CEO. Alongside these story updates, the two also look into how conversations surrounding AI liability and insurance coverage are changing.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For official legal advice on an...
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April 16, 2026 • 41 mins
This week, Dave and Ben revisit Anthropic’s lawsuits against the Pentagon after the company was reclassified as a supply chain risk. Additionally, Dave and Ben also take a look at the looming Section 702 deadline, which is set to expire on April 20th.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For official legal advice on any of the topics we cover, please co...
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April 9, 2026 • 37 mins
This week, Dave and Ben look into two stories. The first involves how cyberwarfare has become increasingly privatized and the dangers this trend can pose. The second looks into Flock Safety cameras and why cities in Georgia are looking to potentially shut down the company's systems.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For official legal advice on any of the ...
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April 2, 2026 • 40 mins
This week, Dave sits down with N2K's Lead Analyst, Ethan Cook, to talk about the ongoing lawsuits between Anthropic and the federal government after the Trump administration designated the AI firm as a supply chain risk. Additionally, the two also take a look at a new cyberattack insurance program the federal government is currently seeking public comment on.
While this show covers legal topics, and Ben is a lawyer, the views exp...
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March 26, 2026 • 38 mins
This week, Ben sits down with N2K's Lead Analyst, Ethan Cook, to discuss the Trump administration's new national AI framework. The framework covers a variety of key areas such as minor protections, IP rights, and federal preemption. Additionally, the two discuss the FCC's recent import ban of any new foreign made routers due to security concerns.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not ...
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March 19, 2026 • 35 mins
In this milestone 300th episode, Ben has the story on the latest legislative battle over reauthorizing Section 702, as lawmakers once again debate the future of a key U.S. surveillance authority. Meanwhile, Dave covers a new New York state bill that aims to restrict the use of AI chatbots in areas traditionally handled by licensed professionals, highlighting growing concern over AI’s role in sensitive services.
While this sh...
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March 12, 2026 • 42 mins
This week, Dave talks with Jean-Paul Bergeaux, CTO for Federal for GuidePoint Security, about OMB rescinding two Biden era orders, which had mandated that agencies require a software bill of materials (SBOM) from software vendors. Ben shares a follow-up story on the Anthropic/Pentagon dustup. Dave has the latest on the new National Cyber Strategy from the White House.
While this show covers legal topics, and Ben is a lawyer, the...
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March 5, 2026 • 37 mins
This week, Ben sits down with N2K's Lead Analyst, Ethan Cook, to discuss the recent fallout between the Pentagon and Anthropic. The deal between the two soured over the past week, leading to Anthropic being dropped by the government for contracting jobs. Shortly afterwards, the government inked a similar deal with rival AI company, OpenAI.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constit...
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February 26, 2026 • 51 mins
This week, Ben and Dave sit down with N2K's Lead Analyst, Ethan Cook, to discuss the Supreme Court's decision to overturn the Trump administration's tariffs, imposed under the International Emergency Economic Powers Act (IEEPA). Additionally, Dave sits down with Jeff Williams, Founder of OWASP and Co-Founder/CTO of Contrast Security, to discuss how NIST is rethinking its role in analyzing software vulnerabilities as the EU launche...
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February 19, 2026 • 46 mins
This week, Ben and Dave sit down with N2K's Lead Analyst, Ethan Cook, to discuss the 21st annual State of the Net conference. This conference is a series of roundtable panels and interviews where industry experts and lawmakers meet to discuss the most pressing challenges facing the technology environment today. Throughout this conversation, our team breaks down AI, electricity grid stability, and media mergers. We also have some fo...
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February 12, 2026 • 41 mins
This week, Ben has a story on An AI-run social network exposed API keys, raising fears of agent hijacking and corporate data breaches. Dave's got the story of a judge tossing a case after a lawyer repeatedly filed fake AI-generated citations, calling it a failure of basic legal research.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For official legal advice on a...
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February 5, 2026 • 59 mins
This week, we are joined by Tony Scott, CEO of Intrusion and former federal CIO, sharing his perspective on evolving regulation and the realities behind critical policy shifts. Ben has a story on the promise of AI to automate compliance. Dave's got reports that the Trump administration plans on using AI to write federal regulations.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constit...
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