Students with learning disabilities (LD) comprise an increasing portion of the university population. These students often face a disproportionate host of educational and attitudinal challenges, including dysgraphia, ADHD, reading comprehension issues, problems with information retention, and learned helplessness. Current instructional practices may not address obstacles faced by these students. In this study, students with LD will verbalize their thought processes and strategies as they work through a confidence interval word problem. We first identify several primary obstacles to student success. We also explore students’ response patterns and their attempts to use aids to overcome obstacles. By gaining an improved understanding of how learning disabilities affect students’ efforts toward statistical problem solving, we hope to develop more effective methods to sustain statistical literacy for their long term success.