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Explore the challenges of automating legacy desktop applications in this 24-minute conference talk from RubyConf 2021. Dive into the world of enterprise software where complex, outdated systems still play crucial roles in business operations. Learn how to tackle the daunting task of testing and modifying these applications without access to their internal workings. Discover a innovative approach using Windows VM, screenshots, image recognition, and Minitest to create a custom Robotic Process Automation (RPA) framework. Gain insights on leveraging JRuby and Sikuli to interact with legacy software, ensuring that even minor changes don't disrupt critical business processes. Perfect for developers and IT professionals dealing with the maintenance and modernization of enterprise-level desktop applications.