The present study focuses on the level of stress a teacher perceives when dealing with the most behaviorally challenging student in his or her classroom. To measure stress in Dutch elementary classrooms, a sample was drawn of 582 teachers. Two questions concerning this relation between student and teacher will be addressed. First of all, we focus on background variables of teachers and students as sources of variation in explaining the magnitude of challenging student behavior and the associated level of stress teachers experience. The second topic of this paper is to accommodate the potentially stressful relationship between student and teacher in a wider network of surrounding variables, which are, Self-efficacy, Negative affect, Autonomy in taking decisions, and Support amongst colleagues. To evaluate the presence of challenging behavior, the behavior of the student is related to more general variables like student responsibility, class size and ratio of boys to girls. We close our paper by assessing the validity of the studied relationship between teacher and student with respect to possible burnout.