The present paper examines a strategy intended to facilitate mathematics learning by adapting the context of instructional material to students’ backgrounds and interests. In four validation studies, the strategy was implemented through teacher management, using college students learning statistical probability rules as subjects. Achievement and attitude outcomes consistently favored treatment groups who received the adaptive contexts over control groups. The culmination of this research is the development of a computer-assisted model to increase the strategy’s practicality and sensitivity to learner differences. The computer model uses stored information about each student to personalize explanations and story examples on a fractions unit.