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Richard Palczynski, leader of the Transpennine Route Upgrade (TRU) project, had devoted the better half of the past five years to co-championing this project with senior leadership at Network Rail, the United Kingdom's national rail operator. The project was now moving full steam ahead, with major vendor contracts worth billions in the process of being vetted and decided on before year's end. However, there had also been major setbacks. Palczynski found himself dwelling on a major blockade (a temporary stoppage in rail service) that had almost been canceled because a lift had not arrived on time. The schedule and financial ramifications were potentially severe, and the TRU suffered major reputational damage. To figure out where the planning had gone awry, Palczynski contacted Dev Amratia, CEO of nPlan, which he had just partnered with for the rest of the TRU. nPlan was tasked with implementing a new framework to manage schedule risk using artificial intelligence (AI), and as it turned out, its framework would have flagged the lift issue and potentially avoided the schedule, financial, and reputational damage the blockage change had caused. In this field-based case, students are introduced to several approaches to project planning, highlighting especially quantitative schedule risk analysis (QSRA) and artificial intelligence schedule risk analysis (AI-SRA), with explorations of cognitive and behavioral biases common in planning. At the Darden School of Business, it is taught in the Executive and full-time MBA 'Project Management' course.