The learning space that online distance learners enter is critically important. The space provides access to learning activities, but it also establishes an environment in which knowledge can be effectively co-created and shared. Designing the learning space involves making decisions about intent, pedagogical priorities, and technological affordances. Online learning spaces communicate educational and social intent and must be designed around the interests, concerns, and cultures of their users. However, the learning space must also embody the vales and perspectives of the instructor/facilitator and the institution that offers the educational experience. This case study presents two situations in which learning spaces were created for specific online courses offered for distinctive learner populations: international students in a Cross-Cultural Management course and U.S. military members enrolled in a Management and Organizational Design course. To explain how these learning spaces were constructed, the case study presents a brief evolutionary history of distance learning and virtual learning spaces. It analyzes two design contexts using an organizational-educational-pedagogical approach. The analysis incorporates differing learner anticipations, concerns, and cultural perspectives and invites the reader to consider appropriate learning space design. This case study also encourages readers to consider their own solutions to these specific learning space challenges. Recommendations and suggestions are made about the ways in which these specific cases might be generalized to different contexts.