As synthetic media becomes more convincing, cyber risk is expanding beyond our systems and into perception itself. Impersonation events challenge the architecture of "traditional" cyber insurance, which is built around technical failure and security events. In this episode of The Cyber Periscope, Pam Signorello sits down with Michael Phillips, Head of Global Cyber Portfolio Underwriting at Coalition, to explore how synthetic media is reshaping cyber risk, why deepfakes present unique challenges for insureds and insurers alike, and what the emergence of Coalition's dedicated Deepfake Response Endorsement signals about the future of cyber insurance. From reputational harm to the erosion of digital trust, this conversation examines how underwriting, coverage structure, and risk assessment are evolving in the age of AI.

As cyber operations increasingly intersect with geopolitical conflict, legacy insurance exclusions are being put to the test. In this episode of The Cyber Periscope, Pam Signorello sits down with Jessica Gallinaro to unpack how modern cyber incidents are challenging decades old assumptions about the war exclusion. Together, they explore why legacy policy language struggles to address conflicts that unfold in the digital realm, how insurers are revising exclusions to reflect real world risk, and what attribution means in an era where military and cyber boundaries continue to blur.

What determines whether a ransomware event becomes a controlled disruption or a full blown crisis? In this episode of The Cyber Periscope, Pam sits down with Dr. Stephen Boyce, CEO and President of The Cyber Doctor, and Don Wyper, COO of DigitalMint, to explore why ransomware outcomes diverge so dramatically. From leadership readiness to the shrinking role of reputational risk, they break down how decisions made months before an attack, and in the pressure cooker moments after, ultimately define the fallout.

What happens when the familiar faces of trusted clients, coworkers, and peers turn out to be AI-generated imposters? In this episode of The Cyber Periscope, Pam Signorello sits down with Nate Lovett of Wiley's Cyber Insurance practice, to dissect the rise of AI-driven cybercrime. From multimillion-dollar deepfake scams to automated ransomware and hyper-targeted phishing, AI has introduced a range of new, rapidly evolving threats for insurers to navigate. Together, Pam and Nate explore why organizational defenses are lagging, how insurers are adapting policy language, and what this next wave of digital crime means for risk management.

Welcome to the premiere episode of The Cyber Periscope, where Pamela L. Signorello sits down with Bill Knauss, special counsel in Wiley's Insurance Practice, to discuss the 2025 NetDiligence Cyber Claims Study, the evolving landscape of cyber risk, the outsized impact of ransomware, and a pivotal court decision challenging the concept of "direct" causation in a cyber insurance policy.