Research on Information Systems (IS) habit formation has been focused mostly on IS habit’s effect on IS continuance. Antecedents of IS habit formation, as reported in the literature, are primarily on users’ prior behavior and comprehensiveness of usage. Most of the literature focus on analyzing the relationship between users’ IS usage behavior and IS habit. Limited work has been reported to investigate genuine and practical ways to develop IS habit, as well as to address the issue of sporadic IS usage, which leads to different interpretations on IS habit and continuance. This study purports to address the theoretical gap on issues related to IS habit antecedents and sporadic IS usage habit in the educational context. Adopting an empirical survey in universities’ (sub-degree and postgraduate settings) learning systems usage, data from cross-sectional survey on learning systems usage on per-course basis is analyzed. Theoretically, our results suggest that IT functionality design (personalization) and social factor (peer effect) have strong and positive relationship on IS habit with respect to the sporadic usage nature of course based learning systems. Practically, we suggest some dimensions for teachers on curriculum design that facilitate IS habit development, e.g., maintaining an online community with substantial student peer input at the early stage of a course.