2025 Midyear Cyber Risk Report

In this webinar, we’ll explore the following key themes we’ve seen emerge and expect to continue throughout 2025:

1. Attackers are working smarter, not harder.

Ransomware attacks are becoming more costly and disruptive, with average claims rising to $1.18M in 2025 and double extortion now a standard tactic, despite most victims avoiding ransom payments.

2. AI is making social engineering more effective.

AI-driven phishing and browser-based attacks are fueling a surge in breaches, driving massive credential theft and making social engineering a leading cause of losses in 2025.

3. Ecosystem risks are connected—and compounding.

Vendor and subsidiary risks drive cascading losses across interconnected businesses, underscoring the need for greater visibility to reduce the probability and impact of widespread disruptions.

Jud Dressler  |  Director, Risk Operations Center

Judson Dressler is the Director of the Risk Operations Center. Dressler recently joined Resilience after serving 20 years in the U.S. Air Force. He was previously the Permanent Professor and Head of the Department of Computer and Cyber Sciences at the United States Air Force Academy, where he taught more than 1,200 cadets each year and conducted long-term artificial intelligence and cybersecurity research. He served as the Commander of the 835th Cyberspace Operations Squadron, where he led 134 cyber airmen to conduct threat-focused, intelligence-driven defensive cyberspace operations. Dressler holds a PhD in Computer Science from Rice University and a Master's in Computer Science from the U.S. Air Force Institute of Technology.

Jeremy Gittler  |  Global Head of Claims

Jeremy Gittler, Esq., serves as the Global Head of Claims at Resilience. He is responsible for leading a team that delivers responsive, expert, and solutions-focused support to policyholders facing cyber incidents, as well as lawsuits arising from Technology Errors and Omissions and Media Wrongful Acts. Under his leadership, Resilience continues to build on its reputation as the most trusted, innovative partner in the cyber insurance industry. Prior to joining Resilience, Jeremy held senior leadership roles at AXA XL, where he oversaw both the U.S. Cyber Claims and Underwriting teams. He launched and built the company’s Cyber Claims operations, helping establish AXA XL as a key player in the market. Jeremy began his cyber insurance career at AIG, managing many of the company’s most complex cyber and technology-related claims. Earlier, he practiced litigation at a leading national law firm, where he developed the legal foundation that informs his strategic and pragmatic approach to managing cyber risk. He holds a J.D. from the Benjamin N. Cardozo School of Law and a B.A. from Emory University.

Maria Long  |  Chief Underwriting Officer [Moderator]

Maria Long is the Chief Underwriting Officer at Resilience. With 18 years of combined experience in insurance, Cyber and Technology E&O underwriting, and strategic portfolio management, Maria Long has played key roles in shaping underwriting direction and advancing risk strategies across the cyber insurance landscape. Throughout her collective career, she has led the design and execution of enterprise-level programs focused on cyber maturity, underwriting innovation, and sustainable portfolio performance.

Maria’s background in leadership, risk analysis, and risk management supports the forward-looking perspective required to drive underwriting strategy while balancing innovation with discipline to support long-term sustainability. She holds a Master of Science in Leadership from Purdue University and is a Certified Information Privacy Manager (CIPM). Her previous roles include underwriting and cyber strategy positions at Munich Re, Allied World, and The Hartford.