Caveat

Latest Episodes:

Trump’s AI Preemption Playbook. May 07, 2026

Show notes

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 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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This week's Caveat Briefing dives into several new deals established between the Pentagon and major frontier AI models aiming to provide advance AI tools and avoid vendor locks. Curious about the details? Head over to the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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All rise for the Chatrie. Apr 30, 2026

Show notes

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 of the topics we cover, please contact your attorney.

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Supreme Court signals location data searches should require a warrant.

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This week's Caveat Briefing ⁠⁠looks⁠ at Brazil's new investigation into Google's AI Overview practices and their impacts on published content. Curious about the details? Head over to the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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Section 702 survives for now. Apr 23, 2026

Show notes

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

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This week's Caveat Briefing ⁠looks at the Indian government's recent move to drop its sixth attempt to force smartphone makers to pre-install state owned applications. Curious about the details? Head over to the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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Anthropic vs Washington. Apr 16, 2026

Show notes

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 contact your attorney.

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This week's Caveat Briefing highlights a recent meeting convened by the Treasury Department concerning security risks related to Anthropic's new model. Curious about the details? Head over to the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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Privatizing cyberspace. Apr 09, 2026

Show notes

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 topics we cover, please contact your attorney.

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This week's Caveat Briefing covers a recent major FBI breach that could have potentially exposed sensitive law enforcement data. Curious about the details? Head over to the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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Reversing the risk label. Apr 02, 2026

Show notes

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 expressed do not constitute legal advice. For official legal advice on any of the topics we cover, please contact your attorney.

Links to today's stories:

Get the weekly Caveat Briefing delivered to your inbox.

Like what you heard? Be sure to check out and subscribe to our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, a weekly newsletter available exclusively to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K Pro⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ members on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K CyberWire's⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ website. N2K Pro members receive our Thursday wrap-up covering the latest in privacy, policy, and research news, including incidents, techniques, compliance, trends, and more.

This week's Caveat Briefing a landmark ruling in a civil case that found both Meta and YouTube liable for damages caused to a user. Curious about the details? Head over to the ⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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Round three: The fight over AI preemption. Mar 26, 2026

Show notes

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 topics we cover, please contact your attorney.

Links to today's stories:

Get the weekly Caveat Briefing delivered to your inbox.

Like what you heard? Be sure to check out and subscribe to our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, a weekly newsletter available exclusively to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K Pro⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ members on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K CyberWire's⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ website. N2K Pro members receive our Thursday wrap-up covering the latest in privacy, policy, and research news, including incidents, techniques, compliance, trends, and more.

This week's Caveat Briefing covers the a recent lawsuit from a coalition of state attorney generals regarding the DoJ's approval of HPE's acquisition of Juniper Networks for $14 billion. Curious about the details? Head over to the ⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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Section 702: The debate continues. Mar 19, 2026

Show notes

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 constitute legal advice. For official legal advice on any of the topics we cover, please contact your attorney.

Links to today's stories:

Get the weekly Caveat Briefing delivered to your inbox.

Like what you heard? Be sure to check out and subscribe to our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, a weekly newsletter available exclusively to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K Pro⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ members on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K CyberWire's⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ website. N2K Pro members receive our Thursday wrap-up covering the latest in privacy, policy, and research news, including incidents, techniques, compliance, trends, and more.

Head over to the ⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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The SBOM where it happens. Mar 12, 2026

Show notes

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 advice on any of the topics we cover, please contact your attorney.

Links to today's stories:

Get the weekly Caveat Briefing delivered to your inbox.

Like what you heard? Be sure to check out and subscribe to our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, a weekly newsletter available exclusively to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K Pro⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ members on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K CyberWire's⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ website. N2K Pro members receive our Thursday wrap-up covering the latest in privacy, policy, and research news, including incidents, techniques, compliance, trends, and more.

This week's Caveat Briefing covers kids' online safety proposals and Anthropic's suit against the Pentagon. Curious about the details? Head over to the ⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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The Pentagon's AI ultimatum. Mar 05, 2026

Show notes

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 cover, please contact your attorney.

Links to today's stories:

The Pentagon bans Anthropic.

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Like what you heard? Be sure to check out and subscribe to our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, a weekly newsletter available exclusively to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K Pro⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ members on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠N2K CyberWire's⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ website. N2K Pro members receive our Thursday wrap-up covering the latest in privacy, policy, and research news, including incidents, techniques, compliance, trends, and more.

This week's Caveat Briefing covers the conflict between Iran, the US, and Israel. As this conflict has continued to intensify, cyberspace has emerged as a key battleground. Curious about the details? Head over to the ⁠⁠⁠⁠⁠Caveat Briefing⁠⁠⁠⁠⁠ for the full scoop and additional compelling stories.

Got a question you'd like us to answer on our show? You can send your audio file to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠caveat@thecyberwire.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Hope to hear from you.

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