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
Expanding the digital evidence trail.
This week, Dave and Ben look at two court cases where one involves a judge ruling that law enforcement's use of Flock cameras was unconstitutional and another where the AI chat logs were used as evidence to levy felony charges. Additionally, Dave sits down with Meredith Burkart, Senior Director of Government Affairs and Public Policy at Halcyon, to discuss how ransomware attacks could be consider
Anthropic’s court battles.
This week, Dave and Ben look at the recent court ruling which has supported the Trump administration's reclassification that Anthropic was a supply chain risk. Additionally, the two look at how AI chat prompts are being increasingly used for gathering evidence for AI-related investigations.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constitute legal adv
When digital tools get it wrong.
This week, Dave and Ben sit down to look at a recent court ruling which has rejected limits on cell phone border searches. Additionally, the two look at another case where a woman was falsely accused of bank robbery after an AI facial recognition system misidentified her and is now suing for $10 million.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not constit
The battle for AI regulation.
This week, Dave and Ben sit down with N2K's lead analyst Ethan Cook to look at the growing calls to enact AI regulations both within the US and across the globe. Spurned on by recent model escapes, policymakers and AI developers alike have steadily begun to call for greater legislative oversight; however, the federal government shows little signs of taking meaningful action.
While this show cove
Addressing the social media algorithms.
This week, Dave and Ben look at how AI and social media are coming under greater regulatory scrutiny. For AI, conversations people are having with their chatbots are beginning to find their way into court cases while Australia looks to continue its crackdown on how social media platforms engage with their users.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not
Flipping AI’s kill switch.
This week, Dave and Ben look at two major AI stories. The first involves Anthropic winning one of its legal challenges regarding the Pentagon designating the company as a supply chain risk. The second story looks at a recent law introduced in Congress that seeks to give CISA the power to force AI kill switch adoption.
While this show covers legal topics, and Ben is a lawyer, the views expressed
Breaking big tech’s hold.
This week, Dave and Ben look at California's latest effort to restrict social media companies further by banning design features that are considered harmful to minors. Additionally, the two discuss recent calls on the Maryland government to investigate data brokers which could be violating state privacy laws.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not co
When companies can hack back.
This week, Dave and Ben discuss how the Trump administration has dramatically changed the cybersecurity landscape after signing a new memorandum, which allows private companies to hack malicious threat actors. Additionally, the two look at the concept of "AI constitutions," and what these policies entail.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not const
Surveillance rulings and social media scrutiny.
This week, Ben and Ethan discuss two major stories. The first looks deeper into the Supreme Court's recent ruling on the Chatrie case and the long-term impacts this decision could have on privacy within the nation. The second dives into another court case decision, which exposes social media companies to greater liability for allegedly addictive design features on their platforms and those featu
Tracking people, training AI.
This week, Ben and Ethan discuss two major stories. The first involves an incident where a police officer was abusing his access to Flock camera databases to track a former partner's movement. The second looks at recent research that found that Chinese military research units have been accessing US frontier AI models to train their own models through a process called model distillation.
While th
AI’s latest security wake-up call.
This week, Dave and Ben discuss two major stories. The first story assess the recent incident where a rogue OpenAI agent escaped its environment and successfully targeted Hugging Face. Additionally, the two also look at an incident where a man was targeted after he reportedly wiped his phone using GrapheneOS.
Afterwards, Dave sits down with Asha Palmer, SVP of Compliance Solutions at Skillsoft,
AI’s political and copyright reckoning.
This week, Dave and Ben look at two stories centered around AI. The first involves how politicians are trying to combat how AI chatbots spread inaccurate or incomplete information on their campaigns to voters. The second story looks at how existing copyright laws are not robust enough to handle how AI models are ingesting content.
While this show covers legal topics, and Ben is a lawyer, the view
The future of transatlantic data sharing.
This week, Dave and Ben look at how the Supreme Court's recent decision could impact data-sharing efforts with the European Union (EU). Additionally, they discuss how the LA Police Department has let its contract with Flock expire after reports emerged that the company was found to be investigating and surveilling innocent people.
While this show covers legal topics, and Ben is a lawyer, the view
AI sovereignty and surveillance.
This week, Dave and Ben examine two developments shaping the future of technology policy. First, they break down the European Union's proposed Cloud and AI Development Act and what it means for technological sovereignty and global competition. Then, they turn to the US, where advances in surveillance, facial recognition, and digital tracking are rapidly expanding government and commercial monitori
Drawing a digital line for geofencing.
This week, Dave and Ben take a look at the Supreme Court's recent ruling that has significantly changed how the law enforcement must approach collecting user location data. Alongside this conversation, Ben also sits down with former Congressman and current President of Americans for Responsible Innovation (ARI) Brad Carson to talk about how US/China trade relations could shape the future of AI dev
Encore: HR1 and the future of U.S. tech security.
We hope you enjoy this encore of Caveat while our team is away.
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 la
A world without Section 702.
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 co
Changes to US AI policy landscape.
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 c
Florida vs OpenAI.
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 topi
The bipartisan case for CISA.
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
Scam ads, AI hallucinations, and legal implications.
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. F
Sony's failed attempt to stop piracy.
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 v
Trump’s AI Preemption Playbook.
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.
Whi
All rise for the Chatrie.
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
Section 702 survives for now.
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 advi
Anthropic vs Washington.
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 t
Privatizing cyberspace.
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 o
Reversing the risk label.
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,
Round three: The fight over AI preemption.
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
Section 702: The debate continues.
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
The SBOM where it happens.
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 leg
The Pentagon's AI ultimatum.
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,
Trump's tariff battle.
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
Wired for the future.
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
Another week, another AI story.
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.
The algorithm is writing the rulebook now.
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
Compliance in the age of surveillance.
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
The expanding reach of surveillance.
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 expre
Consent is not optional.
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 sho
Your data, your rules.
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, a
![The existing state of regulation. [CISOP]](https://megaphone.imgix.net/podcasts/8fb4b698-cdee-11ef-87d9-17bdea2cd7d0/image/4576c79a6260b29daaff0ea0480913c0.png?ixlib=rails-4.3.1&max-w=3000&max-h=3000&fit=crop&auto=format,compress)
The existing state of regulation. [CISOP]
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
Caveat Live: FBI and KU Cybersecurity Conference.
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
Cyber lessons from the frontlines.
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 of
One nation, two AI futures.
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 off
Jumping into a time machine.
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
Red, white, and for you page.
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
AI arms race meets nation-state mayhem.
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
Where are we going with warrantless searches?
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 prosecu
Face to face with controversy.
Today we are joined by Dr. Sasha O'Connell, Senior Director for Cybersecurity Programs at Aspen Digital, discussing "10 Years of Cybersecurity Progress & What Comes Next." Ben talks about a couple of instances of AI companies reigning in their chatbots. Dave's got the story of ICE’s controversial facial recognition operations.
While this show covers legal topics, and Ben is a lawyer, the views e
Cybersecurity on the ballot in California.
Next week, California will hold a major election on Tuesday, November 4, amid heightened cyber risk and increased exposure to potential attacks. With the ongoing government shutdown and reduced grant funding for local counties overseeing the elections, vulnerabilities are growing. Sanny Liao, Co-Founder and CTO of Fable Security, joins to discuss the biggest cyber threats to this election, how att
How North Korea strikes and survives.
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 off
Ghosts on screen.
This week, while Dave is on vacation, Ben Yelin, and Ethan Cook, N2K's Lead Analyst and editor of the Caveat newsletter, take the lead and share their stories. Ben's story is on the legal and ethical issues surrounding Sora, the tool being used to make AI-powered videos of deceased celebrities. Ethan covers the story about Taiwan’s security bureau releasing a new report detailing recent Chinese ha
From alerts to aborts.
Will Daugherty, US Head of Norton Rose Fulbright's Cybersecurity practice, discussing the upcoming expiration of CISA 2015. Ben discusses Apple’s decision to remove the ICEBlock app after pressure from the White House. Dave's got the story of the Secretary of Defense dialing back cyber training fro troops.
While this show covers legal topics, and Ben is a lawyer, the views expressed do not consti
AI on the witness stand.
Sarah Graham from the Atlantic Council’s Cyber Statecraft Initiative (CSI) discussing their work and findings on "Mythical Beasts: Diving into the depths of the global spyware market." Ben has the story of law enforcement agencies increasingly relying on AI to synthesize digital evidence. Dave's got the story of the Secretary of Commerce pressuring Taiwan over ship manufacturing.
While this sho
Red, white, and for you page.
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
Decrypting the future.
Today we are joined by Rebecca Krauthamer, Stanford Quantum Computing Researcher and CEO of QuSecure, to discuss the National Quantum Cybersecurity Migration Strategy Act. Ben has the story of a new California bill regulating AI. Dave's got the story of the controversial technology transfer from the US to the UAE.
While this show covers legal topics, and Ben is a lawyer, the views expressed do
HR1 and the future of U.S. tech security
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 offic
Two seconds to safer online spaces.
Today we are joined by Elad Schindler, Product Manager of AU10TIX, sharing some details about their free assessment tool and readiness guide to help organizations navigate child safety age assurance compliance. Ben discusses some unintended consequences of age verification laws. Dave's got a look at the government’s recent acquisition of a stake in Intel.
While this show covers legal topics, and
Ransomware readiness at risk.
This week, Ben speaks with John Anthony Smith, Founder and CSO at Fenix24, about why law firms are falling behind on recovery readiness as human-operated attacks continue to rise. Ben also shares insights on a hack impacting the federal court system, while Dave takes a look at a Michigan Supreme Court ruling on digital device fishing.
While this show covers legal topics, and Ben is a lawyer, the
Installment plans for your privacy.
On today’s show we are joined by Ron Zayas, CEO of Ironwall by Incogni, to discuss the massive data sharing and privacy risks in the leading Buy Now Pay Later apps. Ben’s got the story of Illinois banning the use of AI in mental health therapy, joining Nevada and Utah in restricting chatbots amid growing concerns about their safety and effectiveness. Dave's got the story of former President Trump
Governments go on the offensive
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 officia
Protecting or policing?
On today’s show Ben’s got the story of how the UK’s new Online Safety Act, billed as a way to protect children, may actually end up doing more harm than good—with mandatory age checks, privacy concerns, and a growing backlash from users. Dave’s got the story of how Flock Safety is expanding its controversial license plate surveillance network into schools—raising serious concerns from privacy advo
Trump’s AI race against China.
While Ben is on vacation this week, Dave welcomes back Ethan Cook to the show. On today’s episode, Ethan breaks down former President Trump’s recently released AI action plan, highlighting key priorities and what it could mean for the future of U.S. tech policy. Dave takes a closer look at the growing bipartisan support for AI regulation in Congress, exploring how lawmakers from both parties are a
The clock’s ticking and the bots are clicking.
This week, Ben's story is on the looming expiration of the Cybersecurity Information Sharing Act (CISA 2015), a widely supported but currently stalled law that enables cyber threat data sharing between the private sector and government, now at risk of lapsing by September 30 due to congressional inaction and conflicting priorities. Dave’s got the story of how a Georgia court's AI-fueled legal blun
Cybersecurity in the states.
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
Who’s the boss of AI?
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
A nation divided can’t stand secure.
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 contac
Cyber offense in the hot seat.
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 o
Answering the cybersecurity call.
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 exp
The art of the breakup: Trump’s antitrust surge.
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 officia
Deep in the tech of Texas.
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 slashi
When AI serves up trouble.
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
Take it down or shut it down?
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
Diving deep into critical infrastructure.
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 officia
iSpy and iDefy.
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
The AI policy divide.
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 express
Big tech, big trouble, and a dash of DORA.
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 gian
The Trump administration’s policy shift.
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 officia
Caveat Live: FBI and KU Cybersecurity Conference.
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
A make-or-break moment for businesses.
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 lawye
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