Collaborative learning environments that support students' problem solving have been shown to promote better decision‐making, greater academic achievement, and more reasonable argumentation about controversial issues. In this research, we developed a technology‐based critical discussion platform to support middle school students' argumentation, with a focus on evidence‐based reasoning and perspective taking. A feasibility study was conducted to examine the patterns of group interaction and individual students' contributions to the critical discussion and their perceptions of the critical discussion activity. We found that more students used text‐based communications than audio, but students who used audio collaborated with each other more frequently. In addition, student engagement in argumentative discourse varied greatly across groups as well as individuals. At the end of the discussion, most groups provided a solution that integrated both sides of the controversial issue. Survey and interview results suggest an overall positive experience with this technology‐supported critical discussion activity. Using the insights from our research, we develop a conceptual dialogue analysis framework that identifies relevant skills under the argumentation and collaboration dimensions. In this report, we discuss our design considerations, feasibility study results, and implications of engaging students in computer‐supported collaborative argumentation.