Education in this digital age is at a pivotal moment, as technological capability, accessibility, and increased financial pressure on educational institutions make online courses particularly attractive for both students and institutions. The growing pervasiveness of online learning across educational sectors brings forth the need to carefully identify the most promising opportunities and widespread challenges for maximizing student experience in online learning environments (Brett, 2016). In this study, three expert practitioners will analyze their research using PeppeR, a web-based collaborative workspace designed to promote learning within an online community. The analysis is meant to elicit recommendations that may be useful for building online courses in which collective meaning-making is an intentional goal. Analyses provide a practical synthesis of research-based insights gained from the daily challenges of over a decade of teaching and learning online. Several themes emerged from the review and emphasize the importance of different aspects of pedagogical design, communication, and evaluation. Different forms of modalities, strategies, and customization in the learning management system are discussed, including personalized messaging, instructor videos, and use of hashtags.