Variable elements of the classroom context affect children’s behavior and may enhance or inhibit task orientation among children who display disruptive behaviors. The current study examined within- and-across-child variation in children’s task orientation, as well as classroom and child predictors of that variation. The sample included 453 preschool children, ages 30–66 months (mean = 48.8, SD = 6.8), identified by teachers as displaying elevated disruptive behavior problems. Children’s task orientation was observed during multiple, 15-min cycles four times throughout the school year using the inCLASS observation system (Downer, Booren, Hamre, Pianta, & Williford, 2010). Results indicated that task orientation varied substantially from cycle to cycle within a school day. The level of teacher involvement as well as the activity setting (e.g., whole group, free play) significantly predicted child task orientation, with greater teacher involvement and teacher-managed activity settings associated with lower task orientation. Children with higher receptive vocabulary and effortful control showed higher average task orientation. The effects of the situational context factors on task orientation varied from child to child, but there was only limited evidence that child characteristics (disruptiveness, receptive vocabulary, and effortful control) or classroom organization moderated the effects of these situational context variables on child behavior: one interaction indicated that children with higher effortful control showed greater task orientation during whole group, but no other interactions were significant. Results are discussed in relation to supporting greater classroom-based task engagement among young children who display elevated disruptive behaviors. (author abstract)