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, including a clear scope of work, specific cybersecurity obligations, rules on data use and model training, indemnification, adequate insurance, and protection against auto-renewal. Listen in for straight talk about negotiating balanced, enforceable terms before signing.

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 highlighting the uncertainty these changes create for policyholders. The conversation emphasizes the importance of realistic expectations about coverage as the gap between rapidly advancing technology and slower-moving insurance frameworks continues to widen.

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 compliance and security improvement.

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 filters. The verdict’s broader significance lies in its implications for thousands of similar pending cases, increased settlement pressure on platforms, and a shifting legal and public focus on social media product design rather than simply content.

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 viewpoints of both parents and corporations, Kevin discusses AI’s growing influences on youth mental health, the importance of responsible design, and the role of parents, professionals, and those seeking to profit from AI.

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 management, credit monitoring, and effective response strategies to mitigate the potential negative results. You won’t want to miss this important episode.

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 scrutinizing AI communications in both criminal and civil contexts. Learn why, in the Heppner case, prompting AI without your lawyer's guidance led to the betrayal of attorney-client privilege, and why, in Warner, a pro se litigant’s use of AI didn’t waive work product protections. These rulings might seem straightforward, but they hold powerful lessons for anyone using AI to handle sensitive legal, financial, or personal information. Listen in for Kevin’s analysis and stay tuned for updates on this increasingly relevant and complex topic.

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 doctrine applied. Hear about why communications with open AI platforms like Claude, Gemini, and ChatGPT aren’t confidential; how courts analyze whether a client is seeking legal advice via AI; and practical steps for attorneys and clients in the era of generative AI. This episode is essential listening for lawyers, compliance officers, and legal tech adopters who want to avoid costly mistakes and leverage AI responsibly. If you rely on AI to assist your legal work—or plan to—listen in.

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 Kevin as he dives into the importance of fact-checking and the implications for legal professionals.

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, auto renewals and termination, indemnification, and insurance. This solo episode emphasizes the importance of clear agreements to mitigate risks associated with vendor relationships.