In this paper, I address a tension that arises from two distinct learner-centered teaching strategies. To provide learner-centered instruction, we are told to invest students in the learning process through providing choices that allow them to exercise their autonomy, and, at the same time, to provide supportive and concrete transparency through narrow, scaffolded assessments. Unfortunately, the very assessment principles that allow us to give clear and transparent standards make it more difficult to allow students freedom over how they meet those standards. I argue here that while there are some strategies to mitigate the practical concerns, the clash between values that this tension reveals can only be addressed by identifying what choices are autonomy-supporting, rather than autonomy-undermining. With a framework in place, I provide examples of strategies that give students both the freedom and the supportive structure they need to learn with appropriate autonomy.