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Explore the evolution of Harvard's CS50 course infrastructure in this 41-minute conference talk. Learn how the course transitioned from a load-balanced Linux cluster to cloud-based virtual machines, then to on-campus VMs, followed by a client-side appliance, and finally to a Dockerized environment. Discover the technical and pedagogical motivations behind each transition, including improved control over infrastructure, easier access to student work, and the ability to scale resources. Gain insights into the benefits of using containers for both student environments and course web applications, such as simplified deployment and service isolation. Examine the successes, challenges, and lessons learned throughout this journey of infrastructure transformation for one of the world's largest computer science courses.