This chapter reports on a pedagogically grounded approach to evaluating course management system extensions. Like many course management systems, Moodle has a range of plugins that can be used to enhance its functionality. Educational institutions are challenged with how to best select and evaluate extensions for potential inclusion within their online learning and teaching platforms. Drawing upon prior course management system and evaluation literature, an evaluation process is presented that incorporates the learning and teaching context, the pedagogical applicability, usability, and overarching considerations as a part of expert review. Applying the evaluation process at Macquarie University resulted in 10 extensions being short-listed from the 749 extensions on the Moodle Community website. The extensions from established educational providers that rated high on pedagogical applicability were deemed the most suitable for adoption. The community building that emerged from the university-wide consultation process was at least as valuable as the evaluation results.