During software updates, preserving or improving the customer experience is of the highest priority. In Gen1, network health was checked manually; an operator would verify no customer impact by checking telemetry dashboards and manually flagging any signs of service degradation. Not only is this practice not scalable but subjecting this critical process to the risk of human error is undesirable as DAA scales and the customer base grows. Therefore, automating and optimizing network health monitoring surrounding software updates is of utmost importance. This paper highlights a data-driven approach to developing and productionizing an automated network health check for use in vCMTS deployment CI/CD pipelines as part of the Gen2 DAA initiative.