This study reviews the literature on the evolution of distance learning in Barbados and Canada's higher education systems in the context of their unique geographies and colonialism. First, postmodern concerns about what is "good" in education (Slaughter, 2001) are considered, followed by a brief discussion of the role of distance learning in neo-colonialism. Next, the evolution of Barbados and Canada's higher education systems within the colonial context is described, setting the stage for the development of distance learning. Both countries' roles within the Commonwealth of Learning organization are compared and used to locate neo-colonial patterns. This analysis highlights risks and benefits of working with external organizations to meet higher education needs in Barbados and Canada, the neo-colonial complexity of a Commonwealth educational organization, and opportunities for strengthening the local while embracing the global in both of these regions.