A central component of online learning, asynchronous discussions have the potential to positively impact distance learners in myriad ways. For discussion to be most impactful, best practices associated with online discussion should be implemented, yet discernment regarding such practices too often remains elusive or unimplemented. To address this need, research-based, high-impact approaches to facilitating meaningful discussions are explored here through 5 different strategies for deepening discussion in the online learning platform. Innovative guidance and support accompany each approach. Furthermore, each exploration into deepening discussion is meant to enhance student engagement and achievement to improve overall retention in online learning.