This chapter illustrates the potential promise and complexities of free college initiatives from the perspective of administrators, faculty, staff, and students who are involved in a scholarship program at a small Midwestern community college. Based on two waves of interviews conducted in 2019 and 2021 respectively, we found that, while largely supportive of the free college movement, the program participants shared clear reservations due to potential unintended burdens on the part of institutions, and compounding barriers for students that free tuition alone cannot solve. This chapter closes by presenting a series of implications to inform the implementation of "free college" to realize its full promise.