Mathematical reasoning is important in conceptual understanding and problem solving. In current reform-based, discourse-oriented mathematics classrooms, students with learning disabilities (LD) encounter challenges articulating or explaining their reasoning processes. Enlightened by the concept of conversational repair borrowed from the field of linguistics, this study designed an intervention program to facilitate mathematical reasoning of students with LD. Conversational repair, an ability to repair communicative breakdowns or inaccuracies, was designed in an implicit–explicit continuum to elicit self-explanation from students with LD in the context of mathematics word problem solving. Using a multiple-baseline across participants design, the study found that the intervention was effective for improving students’ mathematical reasoning and problem-solving ability measured by their self-explanation and word problem–solving performance. It provided implications for future studies concerning the use of conversational repair in mathematics classroom discourse for individuals with LD.