An individual's learning is determined by cognition, motivation, and social context. Taking these aspects into account, we assessed scaffolding in tutoring situations via contingency to determine how successful and unsuccessful teacher-student interactions are shaped. We aimed to find out how the problem-solving process in successful tutoring situations differs from that in unsuccessful tutoring situations with regard to cognition, motivation and increasing task complexity. Therefore, using a qualitatively oriented multi-method approach, we analyzed 26 tutoring situations involving an algebraic word problem in middle schools. Specifically, we analyzed, first, the tutee's independent performance in a transfer task, and second, the tutee's active participation, the activation of participation by the tutor, the impact of errors and the motivational support by the tutor in the tutoring situation. Connecting the results, we composed process graphs and narrative descriptions which revealed three types of successful and three types of unsuccessful teacher-student interaction, depending on the level of the tutee's participation and uncovered cognitive activity (i.e., reactive, collaborative, self-responsible). In successful tutoring situations, the graphs showed high levels of cognitive and motivational support with increasing task complexity. However, in the type reactive participation, motivational support was low. Thus, contingent support should be adapted to the learner's current understanding and task complexity, and motivational support should be administered plausibly for the learner. With this research, we offer a tool to assess contingency regarding cognitive and motivational support in a task-solving process. The results are discussed in relation to the Interactive--Constructive-Active--Passive framework and Cognitive Load Theory.