As higher education institutions move to incorporate more online learning into their long-term strategies, it is important for instructors to become adept at facilitating discussions in ways that engage learners, promote critical thinking, and support the development of a learning community. Through the strategic application of effective discussion prompts, online instructors can facilitate greater student engagement and deeper learning, connecting learners to the course content and to their peers. In this article, the authors discuss the intentional use of five types of discussion prompts used by experienced online instructors to facilitate discussions in an asynchronous case-based course. A detailed description of each prompt is provided, along with specific examples and instances of how to thoughtfully apply each type of prompt during the facilitation of online discussions.