This study explored the use of an online mathematics tutoring system in eight fourth grade classrooms in two Massachusetts communities--a small rural city with a low 2010 Adequate Yearly Progress (AYP) math performance rating and a small suburban district with a high 2010 AYP math performance rating. 165 fourth graders completed 11 modules consisting a pre-test, practice session, and post-test using topics from the Massachusetts math curriculum framework. During practice sessions, students had the choice to consult four online coaches--Estella Explainer, Chef Math Bear, How-to-Hound, or Visual Vicuna--who presented math problem solving strategies from different points of view. Students in both communities showed an average of 23.5% gain from pre-test to post-test across all modules. Girls slightly outgained boys while students below grade level in mathematics performed as well as on-grade level students. Students who used the system in two separate time periods showed a significant mean gain from fall to spring. Visual Vicuna was the most preferred coach, but students in the low AYP community used Estella Explainer and How-to-Hound twice as often in the spring than the fall. Students who completed a pre and post survey showed increased confidence in their ability to do math.