ABSTRACT Research has found that increasing learner control offers several benefits, including increased motivation, attitude, and learning. The goal of the present study was to determine how prior math achievement influences students' selection of the difficulty level of problems within Math Pursuits, a hypermedia learning program. Math Pursuits was designed to help children understand mathematics by discovering how it relates to the world around them. The program presented each learner with an adjustable level of challenge, along with the necessary scaffolding to support success. The researchers hypothesized that students with lower math skills would choose to start with a lower difficultly level; whereas, students with higher math skills would begin the program by choosing a question with a higher level of difficulty. Results supported these hypotheses. This research also examined the motivational framework guiding students' selection of problem difficulty