AI workloads are becoming increasingly complex, with unique requirements around data management, compute scalability, and model lifecycle management. In this session, we will explore the real-world challenges users face when operating AI at scale. Through real-world examples, we will uncover common pitfalls in areas like data versioning, reproducibility, model deployment, and monitoring. Our practical guide will highlight strategies for building robust and scalable AI platforms leveraging Airflow as the orchestration layer and AWS for its extensive AI/ML capabilities. We will showcase how users have tackled these challenges, streamlined their AI workflows, and unlocked new levels of productivity and innovation.