Each emerging digital innovation is a double-edged sword that brings both benefits and risks and challenges that might necessitate new controls. In winter 2024 we conducted a case study at a US business school, to identify GenAI policies incorporated into the design of a planned study-tour course. Students would conduct consulting assign-ments for small Jamaican companies that they would visit during a 10-day trip. This paper is designed to encourage HICSS participants to theorize about a discussion case developed from our study in winter and spring 2024. Together we will theorize about how to balance control and flexibility when pilot-testing emerging digital innovations in education and other contexts, and perhaps set an agenda for future studies.