Justin Reich leads this MIT CMS.595 session on intelligent tutoring systems and adaptive learning technology, part of the Learning, Media, and Technology course at MIT. The discussion traces the MOOC movement's promise to disrupt education through scalable, data-driven, personalized instruction, and examines why that promise has largely gone unmet. Reich and students work through the technical and pedagogical limits of intelligent tutoring systems, including what these systems can measure well, what they miss about how people actually learn, and why personalization at scale has proven harder than early advocates expected. The session runs as a seminar-style discussion rather than a straight lecture, drawing on assigned readings and case examples from existing MOOC platforms and tutoring software. It sits within a broader course examining how digital tools and media reshape teaching, making it most useful to viewers already tracking the earlier sessions on learning technology.