In 1966, Walt Disney tasked a team of Imagineers to build a model of "The Florida Project", a prototype of a planned city designed to leverage the latest technology and innovation to solve some of society's most complex problems, including education. Using this physical model as inspiration and the SAMR model as a foundation, the presenter has engaged in conversations with a number of stakeholders in his district to taking about the the past, present, and future of how classrooms and teachers have evolved to reflect the addition of technology. This presentation will ask the questions “How has new technology allowed education to achieve Walt’s vision?”, “Have we transformed enough?”, and “How can AI help us keep going?”.