This article presents a case study of a two-year pilot to increase pre-collegiate math course success rates at a large community college. The EnableMath pilot involved the use of computerized software that allowed students to practice math problems in a lab during class time. Additional components of the program included the administration of the College Student Inventory (CSI) motivational assessment and in-class counseling support. EnableMath students achieved a course success rate of 15 to 20 percentage points higher than other students in the same math courses. End-of-class survey data as well as enrollment data suggest strong student demand for EnableMath courses. However, for students moving from Pre-Algebra to Elementary Algebra and Intermediate Algebra to college-level (to a lesser degree) courses, success rates for EnableMath students lagged behind other students. EnableMath students moving from Elementary Algebra to Intermediate Algebra achieved similar rates of success as their peers. The article discusses the difficulties in evaluating a non-randomized trial and suggests that the math department focus on improving the transition in pilot sections from Pre-Algebra to Elementary Algebra. (Contains 5 tables.)