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
July 17, 2025 • 45 mins
This week, we are joined by Gary Barlet, former Federal CIO and Air Force Cyber Operations Officer and current Public Sector CTO at Illumio, to discuss how this approach to cybersecurity leaves some states much more at risk than others. Ben has the story of a Virginia case relating to reverse key word searches. Dave's got a highly unusual move by the DOJ against Maryland’s district courts.
While this show covers legal topics, and...
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July 10, 2025 • 49 mins
This week on Caveat, Dave and Ben welcome back N2K’s own Ethan Cook for our latest policy deep dive segment. As our lead analyst, Ethan shares his knowledge of law, privacy, and surveillance on the latest policy developments shaping the cybersecurity and legal landscape.
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 w...
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July 3, 2025 • 42 mins
This week, Ben discusses some major Supreme Court decisions from the just concluded 2025 term. Dave's got the story of a license plate reader company dialing back access after media reports reveal potential oversharing. 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.
Complete our ann...
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June 26, 2025 • 37 mins
This week on Caveat, Dave and Ben sit down with Andy Boyd, former Director of the CIA’s Center for Cyber Intelligence (CCI) and now an operating partner at AE Industrial Partners, a private equity firm focused on national security and aerospace. With decades of experience leading cyber operations at one of the most secretive U.S. intelligence agencies, Andy shares candid insights on the state of offensive cyber operations in the Un...
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June 19, 2025 • 53 mins
Please enjoy this encore of Caveat.
Camille Stewart Gloster, Former Deputy National Cyber Director at the White House, is sharing a retrospective of her public service career. Ben discusses a new lawsuit in Illinois challenging automatic license plate readers. Dave's got the story of an AI hotline between the US and China.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advi...
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June 12, 2025 • 46 mins
This week on Caveat, Dave and Ben welcome back N2K’s own Ethan Cook for our latest policy deep dive segment. As our lead analyst, Ethan shares his knowledge of law, privacy, and surveillance on the latest policy developments shaping the cybersecurity and legal landscape.
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...
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June 5, 2025 • 41 mins
This week on Caveat, Ben’s got the story of Texas becoming the second—and largest—state to pass a law requiring Apple and Google to verify users' ages on app stores and get parental consent before kids and teens can download apps or make purchases, signaling a broader push toward stricter online age checks. Dave dives into the story of President Trump’s 2026 budget proposal, which calls for slashing over 1,000 jobs at CISA and cutt...
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May 29, 2025 • 48 mins
This week on Caveat, Ben’s got the story of a federal judge rejecting Google and Character.AI’s claim that their chatbot’s messages are protected free speech, allowing a wrongful death lawsuit over a teen’s suicide linked to the chatbot to move forward. Dave’s story is on the growing challenges of assigning legal and financial responsibility when autonomous AI agents, increasingly deployed by tech giants like Google and Microsoft, ...
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May 22, 2025 • 39 mins
This week on Caveat, Ben covers growing backlash to a federal proposal that would block states from enforcing their own AI laws for the next decade—a move critics call unconstitutional and a gift to Big Tech. Meanwhile, Dave unpacks the newly signed Take It Down Act, which criminalizes the distribution of nonconsensual intimate images, including AI deepfakes, and requires platforms to remove them within 48 hours. While the law has ...
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May 15, 2025 • 46 mins
This week on Caveat, Dave and Ben welcome back N2K’s own Ethan Cook for our latest policy deep dive segment. As our lead analyst, Ethan shares his knowledge of law, privacy, and surveillance on the latest policy developments shaping the cybersecurity and legal landscape.
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...
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May 8, 2025 • 38 mins
This week, Ben and Dave tackle two major policy stories making headlines. Ben unpacks the Fourth Circuit’s long-awaited ruling in United States v. Chatrie, where the court failed to reach a majority decision on whether geofence warrants violate the Fourth Amendment. Instead, the panel affirmed the lower court’s decision based solely on the good-faith exception, leaving key constitutional questions unanswered. Then, Dave covers the ...
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May 1, 2025 • 42 mins
Please enjoy this encore episode of Caveat.
This week on Caveat, Dave and Ben welcome back N2K’s own Ethan Cook for our latest policy deep dive segment. As our lead analyst, Ethan shares his knowledge of law, privacy, and surveillance on the latest policy developments shaping the cybersecurity and legal landscape.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. ...
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April 24, 2025 • 49 mins
This week we are joined by Avani Desai, CEO of Schellman, who is talking about what we can expect now that Digital Operational Resilience Act (DORA) is in effect. Ben’s got the story of how a federal judge ruled that Google broke antitrust laws to maintain its dominance in online advertising, marking the second major legal blow in a year that could lead to a dramatic restructuring of the tech giant. Dave’s got the story of a Nevada...
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April 17, 2025 • 43 mins
This week on Caveat, Dave and Ben welcome back N2K’s own Ethan Cook for our latest policy deep dive segment. As our lead analyst, Ethan shares his knowledge of law, privacy, and surveillance on the latest policy developments shaping the cybersecurity and legal landscape.
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...
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April 10, 2025 • 57 mins
We've got something special for you this week! We are excited to share our very first Caveat Live event. Host Ben Yelin recently headed to the FBI and KU Cybersecurity Conference at the University of Kansas for a live session of Caveat. During the episode, Ben covered the importance of public/private partnerships with Dr. Perry Alexander. Ben and Professor John Symons spoke about the philosophical issues in AI and how those should ...
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April 3, 2025 • 48 mins
This week, we are joined by Daniel Barber, CEO and Co-Founder of DataGrail, to discuss why data privacy should matter to companies in 2025. Ben has the story of a California lawmaker’s proposal to regulate kids’ use of AI companions. Dave's got the story of a reporter's 300 mile trek through rural Virginia in search of license plate readers.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not const...
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March 27, 2025 • 45 mins
This week, we are joined by Tara Wisniewski, EVP for Advocacy, Global Markets and Member Engagement at ISC2 discussing their work on "Navigating Global Transitions: Cybersecurity's Role Amid Political Change?" Ben and Dave both tackle the questionable and potentially illegal use of Signal by high level Trump officials after a text message got sent to the wrong person.
While this show covers legal topics, and Ben is a lawyer, the v...
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March 20, 2025 • 47 mins
This week, we are joined by David Wiseman, Vice President of Secure Communications at BlackBerry, discussing making CISA's encrypted communications guidelines actionable. Ben's got the story of the UK’s Online Safety Act kicking in, with Big Tech companies like Musk’s X facing massive fines and potential shutdowns for failing to remove harmful content, despite Musk’s hopes that Trump will intervene to water it down. Dave's got the ...
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March 13, 2025 • 43 mins
This week on Caveat, Dave and Ben welcome back N2K’s own Ethan Cook for the third installment of our newest policy deep dive segment. As a trusted expert in law, privacy, and surveillance, Ethan is joining the show regularly to provide in-depth analysis on the latest policy developments shaping the cybersecurity and legal landscape.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute leg...
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March 6, 2025 • 46 mins
Please enjoy this encore episode of Caveat.
This week on the show, Dave and Ben are excited to welcome N2K's very own Ethan Cook, a trusted policy expert, who will be joining regularly for a new segment. Starting this month, Ethan will be contributing every second week to dive deep into the world of law, privacy, surveillance, and more, offering insightful analysis on the latest policy stories.
While this show covers legal topics,...
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