Students with learning disabilities identify teachers' understanding of them as learners as crucial for their empowerment and success in school. This study provides insight into how the analysis of students' academic and social situational tendencies can provide teachers with better understanding of their students' educational experiences and lead to strategic adaptation of instruction. For this qualitative case study, the researchers analyzed the mathematical and social tendencies of an eighth-grade student with a learning disability as well as the support tendencies of a tutor during various tutoring situations. Findings indicated that recognition of patterns of student tendencies between learning situations helped the tutor adapt instruction accordingly to promote an environment conducive to success.