A grounded conversation design approach is posited as a way to study complex conversational processes within online learning environments. This approach is applied to online learning contexts to leverage conversation quality and learning. Study I examines conversations emerging within an online learning community created within an undergraduate class to critically discuss research. Study II applied conversational protocols derived from study I within an undergraduate online editorial board simulation intended to generate critical discourse. The chapter suggests how basic grounded conversation techniques can be applied in a variety of online learning environments to study conversation and develop grounded conversation theory within the context of online learning. Grounded conversation design is based on the assumption that conversation is situated and grounded within the social contexts from which it emerges.