Operations teams have long functioned under a primary mandate of assuring customers the most solid and uninterrupted experience possible. The recent advent of software reliability engineering (SRE) introduced engineers to the formalized automation of toil, leaving more time for creative problem solving of service interruptions. However, twin issues remain: how to automate a virtualized cloud environment in practice, and how to measure and prioritize repeated tasks to be automated for the greatest impact. In this paper, we offer a case study of the evolution of a complex cloud infrastructure from a state of manual deployment, scaling, failover, and upgrading, to one of push-button control and automated self-management. Driving this evolution is a pair of mathematical tools developed in Comcast’s Core Application Platforms (CAP) group that use the financial concepts of “net present value”/NPV and “internal rate of return”/IRR to organize and value automation opportunities simply and objectively.