This chapter proposes a contingency theory based model of eLearning. Using this theoretical lens the authors argue that given a virtual learning environment, there are ideal profiles of eLearning (“fit”) that result from a combination of learner engage- ment, learner style, learning task, and the appropriate leveraging of IT capabilities. Using this theoretical lens, the authors discuss how eLearning technologies can be classified into an eLearning technologies capabilities grid. The chapter concludes with a discussion of the implications of the proposed theoretical model and one illustration of “ideal profile” is described wherein bundles of information technology capabilities were utilized to enhance and augment the learning experience of the students.