Research Findings: This descriptive study examined classroom activity settings in relation to children's observed behavior during classroom interactions, child gender, and basic teacher behavior within the preschool classroom. A total of 145 children were observed for an average of 80 min during 8 occasions across 2 days using the Individualized Classroom Assessment Scoring System, an observational measure that conceptualizes behavior into teacher, peer, task, and conflict interactions. Findings indicated that on average children's interactions with teachers were higher in teacher-structured settings, such as large group. On average, children's interactions with peers and tasks were more positive in child-directed settings, such as free choice. Children experienced more conflict during recess and routines/transitions. Finally, gender differences were observed within small group and meals. Practice or Policy: These findings might encourage teachers to be thoughtful and intentional about what types of support and resources are provided so children can successfully navigate the demands of particular settings. These findings are not meant to discourage certain teacher behaviors or imply the value of certain classroom settings; instead, by providing an evidence-based picture of the conditions under which children display the most positive interactions, they can make teachers more aware of choices within these settings and assist powerfully in professional development and interventions. (Contains 5 tables and 1 figure.)