All technical fields add more automation over time as we replace human labor with innovative technologies. Automation comes with many advantages: It creates research opportunities, offers savings in practice, and reduces errors. Automation also comes with disruptive costs. Processes must change to accommodate the automation, and human laborers must adapt by learning new knowledge and skills. Automation also evolves over time as advances inspire more new ideas for automation. This presentation will reflect on automation through history and on years of experience inventing ways to automate software testing. The talk will review achievements in test automation, discuss challenges in cutting edge domains such as games and AI, and present open problems for future research and for practical applications.