Operating from the margins of the formal curriculum and with relatively limited resources, student orientation faces unique teaching and learning challenges in representing the ideas and values of the academic world in a form that is relevant and engaging for prospective students in the non-academic world outside. Online learning adds a further layer of complexity in the technical medium through which the ideas and values must flow. GetReal, a web-based orientation program for independent use by prospective online/distance students, tackles these challenges with a strategy that moves away from information-based orientation to focus more on the kind of border-crossing practices that enable students to operate at a genuinely independent level among the overlapping contexts of study, technology and personal life. Practices of reality-checking, confidence-building, choosing and self-motivating are enabled through a relatively simple technical concept: the online interactive checklist expanded and elaborated to the point of forming the framework of a whole orientation website and the whole orientation experience. From first moment of contact, the student user stands within a framework that not only assumes active participation in the orientation process but makes it difficult to avoid. The conceptual framework of the GetReal site is outlined and its practical implementation described in relation to content architecture and use of technology. The conceptual vision embodied in the GetReal site provides a framework for discussion on the construction and delivery of student orientation in online and distance learning environments.