The researchers conducted a microanalysis of two purposefully sampled sessions of a tutor working with a student with a learning disability (LD) engaging with multi-step equations with and without fractions. During the tutoring sessions, the student experienced quick, independent success on equations without fractions, but struggled considerably when fractions were embedded in the equations. When the tutor supported the student with gestures, verbal instruction, and managing his work on paper, the student was able to make some progress. The situation described in this study presents challenges for teachers regarding when to let students use a calculator for solving fraction computations versus when to teach fraction concepts as well as how to support a student with an LD who is struggling with possible anxiety while engaging with challenging mathematics.