The researchers conducted a qualitative case study to describe the teaching and learning of a third grade student with a learning disability as he worked on multiplicative tasks with a tutor. The student's strategies, at participatory and anticipatory levels of understanding, were analyzed to inform instructional decisions we made to support the student's work. The teacher and the student utilized manipulatives, gestures, and diagrams to support their conversations about multiplicative situations. The student struggled with some multiplicative situations and the tutor made adjustments to the difficulties of the posed tasks and provided visual support for his memory and processing to respond to these struggles. We describe this student's strengths as a problem-solver and how he thrived when given the supports he needed and the opportunities to think critically as well as his struggles with tasks posed that were not yet within his reach as a learner. We also discuss the complexity of the challenging instructional decisions that teachers have to make with students like the participant in this study.