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Why Ransomware Still Keeps Winning | Adrian Sanabria, Principal Researcher, The Defenders Initiative

13 Nov 2025

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Adrian Sanabria, Principal Researcher at The Defenders Initiative joins Field CISO John Carse to dissect why security keeps failing despite massive investments in tools and compliance frameworks. In this episode, John turns the tables and puts Adrian (also the Main Host of Enterprise Security Weekly) in the hot seat — discussing why focusing on checklists keeps defenders perpetually behind, how cyber insurance might force real change and why AI has become the attacker's number one accomplice in 2025.0:00 On mission-driven security14:10 Cyber insurance as the next control enforcement25:35 Why ransomware is a great framework for attackers33:54 Prompt injection attacks are the next big problem40:29 Using the frameworks in the right way to guide security decisions and communication45:14 Why CISOs must avoid the "hoarding" mindset🔔 Follow Adrian and John on:https://www.linkedin.com/in/adrian-sanabria/https://www.linkedin.com/in/johncarse/🔥 Powered by SquareXDeployed as a lightweight extension, SquareX turns any browser, on any device, into a secure enterprise browser. Find out more about SquareX at https://hubs.la/Q03rPcbf0

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