At Pinterest, there are over 10,000 DAGs supporting various use cases across different teams and roles. With this scale and diversity, user support has been an ongoing challenge to unlock productivity. As Airflow increasingly serves as a user interface to a variety of data and ML infrastructure behind the scenes, it’s common for issues from multiple areas to surface in Airflow, making triage and troubleshooting a challenge. In this session, we will discuss the scale of the problem we are facing, how we have addressed it so far, and how we are introducing LLM AI to help solve this problem.