This multiple case study provides a description and explanation of what, why and how instructional strategies have the potential to promote learning-centered synchronous dialogue online, specifically in the synchronous web-based course system (SWBCS), Elluminate Live! This research was guided by the theory of transactional distance, specifically the dialogue component. Qualitative data collection techniques were employed, including, interviews, observations, researcher's reflective journal, surveys and Delphi. Three cases were examined, consisting of the instructor, their students and the synchronous sessions during the course. Data were analyzed iteratively to garner themes. Member checks were conducted to maintain an active corroboration on the interpretation of data between the researcher and those who provided the data. This study suggests that instructors can promote learning-centered dialogue in the SWBCS by: (a) building social presence, (b) facilitating discussions, (c) providing feedback, (d) assigning group work, (e) respecting diverse talents and perspectives, and (f) emphasizing time on task. The main tools used to implement these strategies in the SWBCS were the duplex audio (VOIP), direct messaging (text chat) and whiteboard. Unique aspects of promoting dialogue in the SWBCS are that it can allow for: (a) relief of communicative anxiety, (b) convenient, inexpensive invitation of guest speakers, (c) facilitation of multiple threads of discussion and (d) extended opportunities to offer office hours. The main tools used to implement these strategies in the SWBCS were the duplex audio (VOIP), direct messaging (text chat) and whiteboard. Two of the three instructors and a majority of the students whom were interviewed perceived the SWBCS effective for implementing instructional strategies that promote dialogue. Further research may examine a greater variety of content areas, more in depth questions of why particular instructional strategies are implemented using the SWBCS or the relationship between dialogue, structure and learner autonomy in the SWBCS.