The Harvest City case describes the implementation of a cloud- and IoT-based intelligent procurement system at a new convention complex in the U.S. Midwest. The decision to build a convention complex is a strategic initiative for this city and involves extensive use of information technology. The risk of implementation failure is high. Such fail ures are costly, highly visible, and affect multiple stakeholders. This case explores the challenges of large-scale, computer-based system implementation by examining the events, decisions, and actions taken to implement the intelligent procurement system at Harvest City. This case helps students to reflect on and discuss the challenges of implementing IT-enabled change initiatives, especially those that requires streamlined and integrated inter-organizational processes. The case discussion gives students insight into what factors influence the success and failure of IT projects.