Best practices in early childhood include using measures to identify children’s social-emotional and behavioral needs within routine, naturalistic preschool contexts. Aligned with best practices, we examined the combined utility of two contextual measures, a teacher report and a direct observation of classroom behavior, in the context of interactions with teachers, peers, and learning tasks. Latent profile analysis (N = 527 children) identified four profile groups: (a) well-adjusted and positively engaged, (b) high externalizing and conflict engagement, (c) adequately adjusted/mildly disengaged in learning tasks, and (d) elevated internalizing behavior and low engagement. Children’s profile classification was associated concurrently with emotion regulation and social competence. Teachers independently reported on children’s social-emotional or academic concerns. Teachers’ reports of social-emotional concerns comported for children in the externalizing profile but did not comport for the internalizing group. Findings illustrate the utility of a contextual assessment approach for early identification and intervention, particularly for children who display internalizing behavior. (author abstract)