This paper examines the nature of the design, layout and management of two pilot post graduate distance learning programs offered at Uganda Management Institute(UMI) and the challenges it so imposes on the quality of the programs within the context of a growing institution. The programs offered are “Project planning and Management”; and “Monitoring and Evaluation of Programs”. The writers explore how Print and online methods are fairing as perceived by the students and tutors on the course, and depict results from interviews carried out with10 out of 12 tutors and also from answers to questionnaires distributed to 100 students during face to face sessions out of 120 supposed to attend. The paper seeks to find out how issues that arise from the evaluation such as inadequate support for the students, a systems failure or unstable internet network, limited interaction between students and tutors, the eminent minimal follow up of students, and generally the institutional inadequate knowledge of the special needs of distance learners compared to the conventional students can be approached and eventually solved. The writers conclude that most challenges that befall the pilot distance learning programs of UMI emanate from the onset design, layout and management of the program as laid down in the proposal to start distance and online studies. There is need to revamp the proposal and develop regulations that befit distance learning of the 21stth century that put the learner at the forefront and technology as unavoidable partner, thus creating a community of learning and a community of learning organization. The impending recommendations are that there is a need for tutors to challenge students enough to cause them to read from their work stations. Secondly tutors training and capacity building workshops should be regular, and for the UMI to realize that in order to build contextual capacity, it is important to bench mark with other institutions if the institution is to start on the process of continuous improvement through the customization of best practices, processes and experiences. Just around the corner distance learning programs use digital libraries, quality content modules, and in built discussion programs are in place to improve on the management and implementation of distance learning. It is in the pipeline that the most immediate solution to challenges so depicted is to accommodate a blended learning system consisting of both online and print based distance learning. // Paper ID: 183