This article proposes an adaption of the Toulmin model of argumentation as a congenial method to investigate interactive political learning processes. The interactive learning environment is provided by the “Found-a-Village” project, where students simulate to establish their own social and political system. I will start my essay by introducing the “genetic” village-setting which works as a trigger for the formation of political judgment and conflict resolution skills. Then, I will define claims, grounds, warrants and premises as basic parts of Toulmin’s model. After presenting six types of politically relevant warrants, I will present a four-level-model for the analysis of political learning processes, distinguishing private, public, institutional and systemic perspectives on politics. Later on, I apply this model by comparing two quite different classes during the initial phase of their village-projects: While the “public” class uses the simulation to seriously negotiate their political values, the second class takes a fairly playful and “private” time-out from typical instruction. Both classes, at a different speed, undergo a continual development from unfounded claims and inadequate arguments to the reflection of their own and opposed political value-orientations. The analysis of implicit parts of individual argumentation confirms the method to be helpful for teachers’ diagnosis skills.