Explore the complexities of test automation in software development through a comprehensive conference talk. Delve into intentional and unintentional compromises, drawing insights from the Jenkins project. Examine the costs, risks, and benefits of automated testing, including its impact on comprehension, confidence, and problem identification. Learn to recognize and manage these costs while maximizing the value of automated tests. Analyze real-world examples of missed issues, undetected problems, and overlooked use cases through the lens of test automation. Gain valuable insights into the software testing pyramid, honeycomb model, initial development, and ongoing maintenance. Address challenges such as untrained users, behavioral inertia, and unintended compromises. Discover strategies for making informed choices in test automation, including when to skip tests and how to implement chaos engineering theories for confident rollbacks.