For administrators who are contemplating an online program, it is vital to know the critical design and administrative issues to consider as well as the decision-making processes one might typically encounter. This paper discusses ten issues that the administrators at Indiana University's Kelley Direct Program (KD) have found most challenging and have had far-reaching implications for the program. In discussing each issue, KD's decision and rationale for that decision are explained and the associated implications are stated. Where appropriate, KD's decisions are compared to the choices made by similar online programs at other universities. Theoretical discussions found in the literature are also incorporated.