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Practice-based teacher education helps preservice teachers address the “problem of enactment” for complex pedagogies like facilitating discussions. Yet, situated theories highlight a parallel “problem of context” (Lave, 1991), where participation is often studied without fully considering its embedded social contexts. This paper analyzes 63 assignment memos from 16 preservice social studies teachers to examine how they conceptualize contextual factors shaping discussion enactment and how macrosociopolitical forces appear in their reflections. Findings show cooperating teachers can enable or constrain enactment; perceptions of students’ identities, particularly of Students of Color, shape expectations for participation; and linking learning to the wider world proves difficult. These insights underscore how context and identity intersect with pedagogical practice in meaningful, often challenging, ways for novice teachers.