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PODCAST

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.

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All Episodes

38:47

Round three: The fight over AI preemption.

Caveat ·

2026/03/26

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 constitute legal advice. For official legal advice on any of the

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35:45

Section 702: The debate continues.

Caveat ·

2026/03/19

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 show covers legal topics, and Ben is a lawyer, the views expressed do not

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42:54

The SBOM where it happens.

Caveat ·

2026/03/12

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 views expressed do not constitute legal advice. For official legal

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37:30

The Pentagon's AI ultimatum.

Caveat ·

2026/03/05

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 constitute legal advice. For official legal advice on any of the topics we

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51:28

Trump's tariff battle.

Caveat ·

2026/02/26

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 launches GCVE.While this show covers legal topics, and Ben is a lawyer,

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46:00

Wired for the future.

Caveat ·

2026/02/19

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 follow up from a friend of the show and former federal law enforcement

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41:37

Another week, another AI story.

Caveat ·

2026/02/12

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 any of the topics we cover, please contact your attorney. Links to

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59:39

The algorithm is writing the rulebook now.

Caveat ·

2026/02/05

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 constitute legal advice. For official legal advice on any of the topics we cover,

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52:54

Compliance in the age of surveillance.

Caveat ·

2026/01/29

On today's episode of Caveat, we are joined by Matt Hillary, Chief Information Security Officer at Drata, discussing how AI is reshaping the compliance landscape and what it takes to build trust at AI speed. Ben has the story of Immigration and Customs Enforcement and their extensive use of modern surveillance tools. Dave discusses the Supreme Court’s taking of a case involving Facebook tracking pixels and video store rentals. While this show covers legal topics, and Ben is a lawyer, the views

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52:55

The expanding reach of surveillance.

Caveat ·

2026/01/22

Today we are joined by Brian McGinnis, partner at Barnes & Thornburg LLP, who is discussing youth protection and data privacy and the Federal Trade Commission. Ben has the story of the Supreme Court agreeing to take up a high-profile case on geofence warrants. Dave takes a look at the global question of digital sovereignty.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

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46:18

Consent is not optional.

Caveat ·

2026/01/15

This week, Ben and Dave discuss the ongoing controversy surrounding Grok and its ability to generate nonconsensual nude images, raising fresh concerns about AI safeguards, consent, and accountability, before turning to a conversation with Caitlin Clarke, Senior Director for Cybersecurity Services at Venable, who breaks down the Cybersecurity Information Sharing Act of 2015 (CISA). While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal advice. For

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35:45

Your data, your rules.

Caveat ·

2026/01/08

On today’s episode, Ben and Dave dive into the wave of new privacy legislation taking effect across the U.S., with California, Texas, and Virginia leading the way. We explore how these laws are giving consumers more control over their personal data—like California’s new “Delete Act” that lets residents remove their information from data brokers in one step. 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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40:00

The existing state of regulation. [CISOP]

Caveat ·

2026/01/01

While our team is out on winter break, please enjoy this episode of CISO Perspectives.Regulation is a double-edged sword. While it helps create structure, establish accountability, and set standards, it also creates unnecessary hurdles, slower response times, and overly rigid systems. With every administration, policy goals and subsequently regulatory stances change, which can have major impacts on business operations. In this episode of CISO Perspectives, host ⁠Kim Jones⁠ sits down with Ben

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54:53

Caveat Live: FBI and KU Cybersecurity Conference.

Caveat ·

2025/12/25

While our team is out on winter break, please enjoy this episode of Caveat.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

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43:01

Cyber lessons from the frontlines.

Caveat ·

2025/12/18

On today’s episode, we welcome back cybersecurity expert Caleb Barlow. Caleb joins us to explore lessons learned from conflicts in Ukraine and Gaza, with a focus on emerging threats to GPS systems and how they could impact security, military operations, and critical infrastructure.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. Get the weekly

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37:00

One nation, two AI futures.

Caveat ·

2025/12/11

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 we cover, please contact your attorney. Policy Deep Dive In

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45:55

Jumping into a time machine.

Caveat ·

2025/12/04

This week, Ben Yelin discusses the new California Opt Me Out Act that requires web browsers to offer a one-click “opt-out” setting that stops companies from selling or sharing your data. Dave Bittner bring the story about the Supreme Court of the United States weighing whether internet service providers must cut off users who repeatedly pirate content — a ruling that could transform how online piracy is policed and overhaul liability for ISPs. Ben and Dave are joined by Daniel Woods, Principal

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57:50

Red, white, and for you page.

Caveat ·

2025/11/27

Please enjoy this encore of Caveat. This week, we are joined by ⁠Michele Kellerman⁠, Cybersecurity Engineer for Air and Missile Defense at ⁠Johns Hopkins University Applied Physics Lab⁠ discussing Women's health apps and the legal grey zone that they create with HIPAA. Ben has the story of the potential sale of TikTok to U.S. investors. Dave's got the story of a looming deadline on renewal of a key cybersecurity information sharing bill. While this show covers legal topics, and Ben is a lawyer,

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44:49

AI arms race meets nation-state mayhem.

Caveat ·

2025/11/20

This week, Ethan Cook, N2K lead analyst and editor of the Caveat newsletter joins Dave and Ben with a rapid-fire download from Public Sector Ignite — from CISA’s strategic pivot to the evolving threat landscape across China, Russia, Iran, and North Korea. He teases major takeaways on quantum risk and the ticking clock to “Q-Day,” why telecoms remain a soft underbelly, and how AI is turbocharging both defenders and attackers.While this show covers legal topics, and Ben is a lawyer, the views

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51:02

Where are we going with warrantless searches?

Caveat ·

2025/11/13

Please enjoy this encore of Caveat.This week, we are joined by ⁠Max Shier⁠, ⁠Optiv⁠'s CISO, to discuss the newly-released CMMC 2.0, Cybersecurity Maturity Model Certification, and how to ensure compliance. Ben discusses a federal court’s decision holding warrantless queries of the Section 702 database unconstitutional. Dave looks at a murder case in Cleveland that’s been derailed by the prosecution’s use of AI. While this show covers legal topics, and Ben is a lawyer, the views expressed do not

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338 results

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