Cyber risk is no longer theoretical. It is operational, measurable, and increasingly accelerated by artificial intelligence. Attackers are moving faster, automating reconnaissance, exploiting third-party weaknesses, and monetizing access with precision. Insurance leaders must understand how these real-world tactics translate into financial exposure and systemic risk. During this session, Tony Rucci will discuss: • How initial access is commonly achieved, including phishing, exposed remote services, default credentials, and compromised vendors. • How ransomware gangs establish persistence, escalate privileges, and exfiltrate data before encryption. • Highlight of notable trends, including lack of network segmentation, unmanaged internet-facing assets, excessive administrative privileges, weak MFA deployment, and overreliance on vendors without meaningful due diligence. • How AI is influencing both attackers and defenders. • Why insurance professionals need to evaluate how insured entities assess vendor controls, contractual security obligations, and AI-driven service dependencies. Participants will leave with a grounded understanding of how attacks unfold in real environments, how AI is changing attacker velocity and defender capability, and how underwriting, risk engineering, and portfolio management strategies can adapt to reflect what is happening to your members.