As data platforms grow in complexity, so do the orchestration needs behind them. Time-based (cron) scheduling has long been the default in Airflow, but dataset-based scheduling promises a more data-aware, efficient alternative. In this session, I’ll share lessons learned from operating Airflow at scale—supporting thousands of DAGs across teams with varied use cases, from simple ETL to complex ML workflows. We’ll explore when dataset scheduling makes sense, the challenges it introduces, and how to evolve your DAG design and platform architecture to make the most of it. Whether you’re migrating legacy workflows or designing new ones, this talk will help you evaluate the right scheduling model for your needs.