Almost six decades since the emergence of Track Two diplomacy, a form of informal and unofficial dialogues between conflicting parties facilitated by scholar‐practitioners, scholarship on the field has grown exponentially. Originally conceived of as a discreet complement to Track One official negotiations between armed actors in conflict, Track Two has become an established and professionalized form of broader conflict resolution. Specific scholarship on Track Two has occupied the liminal space between theory and practice, in which theoretical propositions are often born out of observations from practical applications in empirical cases. Analyzing how Track Two theories reflect these paradigms can give greater insights into the theoretical evolution of the field and where it is headed. This begets a need to regularly and systematically survey the relevant literature on Track Two given the large‐scale changes occurring in its practice. This article discusses the evolution of Track Two theories as embedded in conflict resolution paradigms, namely, strategic bargaining and problem solving; conflict transformation; and liberal and post‐liberal peacebuilding. In particular, I focus on how the recent "normative turn" in conflict resolution literature has impacted Track Two scholarship. Following the analytical framework of a mediation process applied to Track Two scholarship, I organize relevant literature into “generations” and compare what are identified as the main constitutive components of a Track Two initiative in order to understand how the theories have evolved in this second generation of literature. My analysis finds that conceptions of Track Two have moved from “narrow” to “broad”: influenced by a normative imperative toward more inclusive and participatory peace processes in conflict resolution, activities labeled as Track Two have expanded from small, discreet dialogues between unofficial actors to include more robust forms of civil society inclusion and participation.