This chapter contributes to the anthology on technology-enhanced learning in higher education by describing an innovative, Web-based managed learning system. The system is devised to scaffold novice Java (Gosling, 2000) language computer programmers through self-paced learning activities to provide rapid feedback and access to tutorial assistance whenever and wherever a student is ready to learn. This chapter begins with the underlying learning challenges driving the design of a technology-based system to enhance students’ experience of learning to program in Java. It then follows the student-driven, evidence-based development of the system components and presents evidence that the system described is a highly effective technology-enhanced learning environment that positively impacts on student learning experiences and outcomes.