Explore data loss prevention strategies and techniques in this comprehensive conference talk from Louisville InfoSec 2016. Learn about the strengths and weaknesses of DLP tools, how to implement a successful DLP program, and avoid common pitfalls. Discover non-traditional use cases, including employee monitoring and malware hunting. Examine real-world examples, such as the Ashley Madison leak, and learn how to detect cryptomalware ransom notes and string obfuscation methods. Gain insights into building custom malware rules, understanding precise vs. imprecise methods, and implementing DLP countermeasures. Address challenges related to data disorganization, network architecture, and personal vs. professional data. Acquire valuable reference material and management ammunition to enhance your organization's data protection efforts.