This workshop explores the evolution and integration of Artificial Intelligence within Document Management Systems (DMS), tracing its development from legacy optical character recognition (OCR) to contemporary cognitive automation. We analyze the historical trajectory of AI through phases of technological enhancement, specifically focusing on the transition from static archival storage to intelligent, context-aware information ecosystems. The session identifies cutting-edge features currently transforming the DMS landscape, including Large Language Model (LLM) integration for automated metadata extraction, semantic search capabilities, and predictive classification. By examining the synergy between AI and document lifecycles, this presentation demonstrates how these advancements optimize discoverability, ensure regulatory compliance, and redefine organizational knowledge management in the digital era.