The premise of this article is that theoretical frameworks and models are essential to the long-term credibility and viability of a field of practice. In order to assess the theoretical challenges facing the field of distance education, the significant theoretical contributions to distance education in the last century are briefly reviewed. This review of distance education as a field of study reveals an early preoccupation with organizational and structural constraints. However, the review also reveals that the theoretical development of the field is progressing from organizational to transactional issues and assumptions. The question is whether distance education has the theoretical foundation to take it into the 21st century and whether distance education theory development will keep pace with innovations in technology and practice.Distance education methodologies have come into prominence during the last decades of the 20th century. The confluence of the need for continuous learning and unprecedented technological innovation in communications have pushed distance education approaches to the forefront of educational practice. However, whether the leaders of these initiatives are the technically literate or the politically powerful, they generally lack a coherent understanding of distance education practice and the full range of possibilities available to achieve desired outcomes. Senior administrators in higher education have become focused, not on educational issues, but the fiscal implications (i.e., cost savings) of distance education, and technology companies see profits (Feenberg, 1999).Conceptual confusion is created with the advent of new terminology (virtual, open, distributed and distance education), new technologies, new program demands, new audiences, and new commercially competitive providers. These developments present enormous challenges for educators to make sense of the distance educational options available. In the context of current change, competition and confusion, distance educators have an unprecedented opportunity to provide leadership and direction. The challenge is to provide theory that will explain and anticipate distance education practices for a broad range of emerging educational purposes and experiences. The question is whether distance