Recent theory and research suggest that self-regulation is not a unitary set of strategies, and that students may employ different types of self-regulation strategies in ways that correspond with different motivational orientations. In this paper, we describe a situated case study approach to investigate the motivational orientation and self-regulation strategies that an elementary school student with learning disabilities employs as he or she engages in a teacher-assigned academic task in an authentic educational context. The method includes a case analysis that involves triangulating and integrating different types of data in order to construct an in-depth view of the student's flow of situated engagement in a teacher-assigned task. Data sources include: (a) traces of strategies in the student's academic product; (b) direct observation of the engagement process; (c) stimulated-recall interview (SRI) on the engagement process using the observation as a memory trigger; and (d) general interview about the experience and purpose of engagement in the task, self-processes related to learning and school, and self-regulation aptitude. The analysis focuses on the integration of the student's purpose and goals for engagement, self-perceptions and affect, and action possibilities and strategies employed. The paper demonstrates the utility of the situated case study approach for the investigation of motivation and self-regulation in one elaborated case of an elementary school student with learning disabilities. In addition, the paper describes more briefly analyses of seven additional cases of elementary school students with learning disabilities who have different characteristics and who engaged in tasks in different contexts. The paper highlights general insights about motivation and self-regulation of elementary students with learning disabilities in integrated classrooms from the comparison of these different cases.