Abstract: The expanding use of online learning in higher education challenges us as faculty, instructional technologists and administrators to reconsider how we might ensure that what we know about the values of situated learning and social constructivism is integrated into the design and implementation of our new digital learning environments User centered design techniques and design based research are promising approaches to rethinking online academic programs The prototyping experience of one team from a public institution in New York focused on users’ experiences to design a space where learners can engage interactively across the span of their program