Caveat

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. Whil...

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....

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 advic...

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 th...

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 of...

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, a...

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 l...

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 sensi...

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...

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,...

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...

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...

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. F...

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 vie...

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 p...

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 expres...

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...

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...

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...

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 ⁠D...

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 off...

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 offi...

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 pir...

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 ke...

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 b...