This article discusses the multi-faceted challenges experienced by professionals embarking on professional development online. It is argued that the barriers to successful completion identified in the literature reflect the complex, overlapping, and not always supportive social systems in which professional learners are embedded. A "person-in-context" perspective is proposed to examine the situatedness of professional online learning challenges. Indepth interviews with 30 media professionals who started a course, gradually disengaged, and finally, dropped out were completed. The situative analysis highlighted how challenges emerged at the intersection of work, home, and study environments. Three major educational issues for the development of professional online learning are identified: the importance of recognising professional study as an integral part of work; the significance of congruence between online study features and professional learners' characteristics; and, the need for course developers to further enhance their technological and pedagogical capacity in the area of professional online learning.