Since mid-2018, we have used a suite of artificial intelligence (AI) technologies to automatically generate the Association for the Advancement of Artificial Intelligence’s AI-Alert, a weekly email sent to all Association for the Advancement of Artificial Intelligence members and thousands of other subscribers. This alert contains ten news stories from around the web that focus on some aspect of AI, such as new AI inventions, AI’s use in various industries, and AI’s impacts in our daily lives. This alert was curated by-hand for a decade before we developed AI technology for automation, which we call “NewsFinder.” Recently, we redesigned this automation and ran a six-month experiment on user engagement to ensure the new approach was successful. This article documents our design considerations and requirements, our implementation (which involves web crawling, document classification, and a genetic algorithm for story selection), and our reflections after a year and a half since deploying this technology.