An important education issue that needs to be addressed in teacher education is the gap between the continuing and increasing technology demands placed on new teachers entering K-12 classrooms and the training that they receive during their college years. There is evidence that not only are new teachers lacking the technological skills, they also lack the confidence needed to motivate them to expand their technological abilities. There is concern that many school of education faculty are not effectively modeling the use of technology to pre-service teachers in education courses. This paper investigates how the incorporation of the Blackboard Learning System, with its expanded communication and hands-on features, helps pre-service teachers to gain confidence in integrating technology into their future teaching. In addition, it documented how students and professors think the use of a course management system helps students' learning. It will also provide guidance for the effective use of a web-enhanced learning system.