This document is a buyer's guide focused on evaluating Data Loss Prevention (DLP) solutions. It outlines the evolving landscape of enterprise data security, emphasizing the need for modern DLP systems that adapt to changes in how data is created, shared, and consumed. The guide identifies the limitations of traditional DLP approaches, which were designed for a different era and often fail to address the complexities of today's cloud-first and AI-driven environments. It discusses the challenges organizations face, such as the inability to protect sensitive information that lacks recognizable content patterns and the fragmentation of policy management across multiple tools. The guide also presents eight criteria for evaluating DLP solutions, highlighting the importance of a unified policy engine, comprehensive file type support, and the capability to track data lineage across various applications and formats. The goal is to assist organizations in selecting DLP solutions that effectively protect their valuable data in a rapidly changing threat landscape.