Stack Overflow is a mature product with a rich history, and legacy, among the software development community. As Stack has grown over the last 13 years, some of the benefits that have arisen are that users can arrive at an answer to their questions in a number of ways, and the community members have a variety of ways in which they can participate with each other. While this is very desirable, it does lead to complex pathways that users can navigate, and even small changes can have a ripple effect. The Stack Overflow Team had been relying on manual testing for the Teams product for some time but realized they could do a much more effective job by bringing in test automation. In this session, Dale and Meredith will talk about how they automated testing as much as possible, the importance of democratization of testing, how they applied DRY principles to test creation, and how they trigger tests within the release pipeline.