Colleges and universities have increasingly invested in specialized software and hardware designed to enhance and facilitate the instructional process for faculty and students. One type of technological assistance is commonly known as course management software (CMS). Once learned, these CMS packages can greatly enhance and enrich the classroom experience and provide internet based access to course materials, assignments, grades, supplementary materials, such as quizzes, PPTs, and study aids. Like all moderately complex software packages (Blackboard is proprietary software and Moodle is open source software), there is a learning curve involved in mastering the functionality of each CMS. This paper examines the process of changing from one type of CMS (Blackboard) to another (Moodle). Faulty (FT & PT) and students (graduate & undergraduate) were surveyed to obtain opinions about the transition from one CMS system to another. The goal is to identify issues that may be addressed by targeted training and insights which would improve the transition process.