This document summarizes lessons learned about monitoring a data pipeline at Hulu. It discusses how the initial monitoring approach had some issues from the perspectives of users and detecting problems. A new approach is proposed using a graph data structure to provide contextual troubleshooting that connects any issues to their impacts on business units and user needs. This approach aims to make troubleshooting easier by querying the relationships between different components and resources. Small independent services would also be easier to create and maintain within this approach.