Cyber Sip

Erie County in New York State has a new Biometric Transparency and Privacy Act that went into effect June 5, 2026. In this episode, Kevin Szczepanski introduces the new local law—the first such law in New York State—and explains that, according to the law, most commercial establishments in Erie County must stop collecting, storing, using, transmitting, or monetizing customer biometric information....

In this episode, Kevin Szczepanski discusses the potential harms to businesses when they rush into AI vendor agreements without careful contract review. Kevin explains that while AI, biometric, and automation tools can improve efficiency and competitiveness, related contracts often shift major legal, cybersecurity, and financial risks onto the customer. He highlights key provisions to negotiate, i...

In this episode of Cyber Sip , host Kevin Szczepanski and returning guest Kelly Geary explore the growing impact of AI on the insurance landscape, focusing on the rise of AI exclusions in policies and the challenges insurers face in underwriting an evolving risk. They discuss how carriers are proactively addressing “silent AI” exposure through exclusions, definitions, and sublimits while highlight...

In this brief episode, Kevin Szczepanski breaks down the critical importance of cybersecurity risk assessments, explaining legal requirements across industries, what a robust risk assessment looks like, and how organizations must use these insights to bolster their security posture. Aimed at cybersecurity professionals and organizational leaders, the discussion offers practical steps for complianc...

Kevin Szczepanski examines the landmark Kaley G. M. trial, in which a Los Angeles jury awarded $6 million against Google and Meta for harms allegedly caused by YouTube and Instagram use during Kaley’s childhood. This episode explains how the jurors were persuaded to focus not on user generated content but on allegedly addictive platform design features, such as algorithms, engagement loops, and fi...

Based on an American Psychological Association advisory published in 2025, “Artificial Intelligence and Adolescent Well-Being,” and a recent California jury decision that awarded $3 million in damages to a young adult who sued Meta and YouTube, Kevin Szczepanski discusses the impact of AI on adolescent well-being, highlighting risks, legal implications, and necessary safeguards. From the viewpoint...

Do you have a plan for when—not if—someone tries to steal your identity? Do you know the essential steps to take in the first 24 hours, first few days, and beyond? What can you do to protect yourself, your family, and your finances before it happens? Listen in to this fast-paced episode as Kevin Szczepanski breaks down crucial steps to take to protect yourself and respond. Learn about password man...

Are you risking your legal case by chatting with open AI platforms like ChatGPT or Claude? You're not alone, and this episode reveals critical insights that could save your case—whether you're a lawyer, a client, or someone handling sensitive info. In this eye-opening discussion, Kevin Szczepanski dissects two landmark cases—US v. Heppner and Warner v. Gilbarco—that show how courts are scr...

In this episode, Kevin Szczepanski walks through the details of United States v. Heppner. In this landmark case, a federal judge ruled that a client’s use of Claude, an open AI platform, is not protected. As Kevin explains, the court determined that using the AI to “do his own research” exposed the client and waived protections so that neither the attorney-client privilege nor the work product doc...

Kevin Szczepanski is back with a brief solo episode that explores a recent landmark case in New York State that addresses the serious consequences for attorneys and the legal profession of citing fabricated cases and misrepresenting legal sources. The courts, attorneys, and firms large and small must recognize and educate themselves about how AI can both help and hinder courtroom integrity. Join K...

Kevin Szczepanski is back with the debut of Season 5, just in time for international Data Privacy Day and Data Privacy Week. In this first episode of the season, Kevin discusses critical aspects of data privacy and vendor agreements. He outlines five key negotiating points that organizations should consider when entering into vendor agreements, including data-use terms, data-security requirements,...

Kevin Szczepanski welcomes Adam Segal, the Ira A. Lipman Chair in Emerging Technologies and National Security and director of the Digital and Cyberspace Policy Program with the Council on Foreign Relations. They discuss the global AI race, particularly focusing on the launch of DeepSeek’s AI model R1. Kevin and Adam dig into how DeepSeek's advancements surprised many as its open-source model r...

Host Kevin Szczepanski welcomes Damion Walker, managing director of the technology practice for insurance giant Gallagher, to discuss the intricacies of cyber insurance and the newer product, known as tech errors & omissions (E&O) coverage. They explore the evolution of these insurance products, the importance of understanding the differences between them, and how businesses can leverage i...

Kevin Szczepanski welcomes Gregg Davis, managing principal and technical advisory solutions leader at EPIC Insurance Brokers & Consultants. Kevin and Gregg start by discussing the increasing risks of insider threats to cybersecurity and the sophistication of threat actors along with the need for organizations to create a culture of verification and for real-world training. Diving into strategi...

Kevin Szczepanski and guest Nick Reese, co-founder and COO of Frontier Foundry, discuss strategic applications of AI on this episode. Nick’s career evolution includes positions in the US Navy and within the US intelligence community, including a stint as director for emerging technology policy for the US Department of Homeland Security. His company is working on privacy-preserving AI. Kevin and Ni...

Kevin Szczepanski and Michael Kurzer, a partner in the law firm Vinson & Elkins who leads the Technology Transactions & Intellectual Property Group, explore the burgeoning field of AI-ready data centers. Kevin and Michael discuss these data centers’ significance, the complexities involved in their construction and operation, and the legal challenges they face. In addition, Michael shares i...

Kevin Szczepanski and Bob Buda, one of the first-ever certified Oracle database administrators, dive into database design, security, and management. To frame the conversation, Bob asks a hypothetical CEO this question: “What percentage of your annual salary would you wager that your data is totally secure?” He provides background about database design and the critical need for data security. Bob a...

In this episode of Cyber Sip , Kevin Szczepanski welcomes plaintiff-side attorney David Lietz, a senior partner at Milberg. David and Kevin take a deep dive into the complexities of data breach class actions, including their evolution, the risks of identity theft, legal standing, and the settlement process. They note the many reasons people give to not join class actions, also pointing out new met...

Welcome back to Season 4! In this episode of Cyber Sip , Kevin Szczepanski and Kelly Geary, managing principal of Epic Insurance Brokers & Consultants and national practice leader of Professional, Executive & Cyber Solutions, discuss the current state of the cyber insurance market, the impact of AI on cybersecurity, and the challenges organizations face in implementing effective cybersecur...

Welcome to Season 4! In this candid solo season opener, host Kevin Szczepanski shares his personal experience of losing his laptop—and hopes listeners heed the valuable lessons he learned. Join Kevin now for essential steps to take immediately after the loss of a device, including contacting your IT department, changing passwords, and reporting the loss to the police. He also delves into the role...

In this conversation, Sandeep Batta, lead solutions architect for IBM Hyper Protect, discusses the importance of a zero trust cybersecurity model. Sandeep particularly focusses on the rise of digital assets, the implications of quantum computing, and the necessity for organizations to adopt quantum-safe encryption. He emphasizes the need for a secure environment to protect critical data and infras...

Kevin Szczepanski is joined by insurance and technology veteran analyst and author Barry Rabkin as they take a deep dive into all things cyber, cyber risk, and insurability. Barry sets the stage by addressing the evolution of cyber risk and noting that the CrowdStrike outage was both a wake-up call and a harbinger of what’s to come. Kevin and Barry then discuss cyber and operational technology (OT...

Kevin Szczepanski and Brian Haugli, CEO of SideChannel, discuss the implications of the recent CrowdStrike incident. CrowdStrike, an endpoint detection and response (EDR) provider, pushed an update that caused worldwide system crashes and downtime for their customers. Brian and Kevin analyze what happened and look at how CrowdStrike responded. The EDR is still being criticized (and in some cases s...

In this episode, Kevin Szczepanski and Dean Mechlowitz of TEKRiSQ discuss the blind spot that organizations may have when it comes to cyber risks and the need for a cyber risk assessment. They note that the tactics used by criminals to compromise data often don’t require a highly skilled hacker, yet many organizations believe they are secure. Dean emphasizes the importance of conducting a cyber ri...

In a quick solo episode, host Kevin Szczepanski offers practical information that can help when you or someone you know suffers from the modern malady known as identity theft. It’s common and serious, affecting millions of people and costing billions of dollars every year. Most of us know that identity theft happens through various means, such as clicking on malicious links, downloading malware, o...