This case study presents an evaluation pilot of a technology-enabled service, specifically a distance learning program at a university. The primary intent of the case is to illustrate the management of a trial evaluation of an information technology and the need for explicit criteria considering multiple technical and organizational factors. The secondary purpose of the case is to share the learning specific to the administration and delivery of a distance learning program using various media. The distance learning program was conducted on a trial basis with 16 students in a 13-course, 18-month Master of Science in Technology Management (MSTM) program. Compressed video and Internet-based technologies were used for course delivery, in addition to limited on-site instruction. The case study describes the motivation and progression of the trial, up to the point when a decision had to be made about continuing the program beyond the trial. The experience is considered from multiple perspectives, specifically those of the school administration, faculty, and students. Positive and negative aspects are highlighted to lay the groundwork for analysis at the decision point.