Students with an identified specific learning disability (SLD) often struggle with written expression. Assistive technology (AT) is an accommodation designed and implemented by special education teams under an Individual Education Program (IEP) to support students with writing disabilities in the classroom. Speech-to-text (STT) is AT that can assist students with writing difficulties, including students with SLD. Occupational therapists (OTs) are part of the IEP team that implements accommodations, including AT, for students. OTs need research to make evidence-based decisions to support students’ educational needs. In this case report, and OT implemented STT with a student who struggled to handwrite or type written expression assignments. The student completed two narrative writing pieces, one with typing, then after learning STT, a second with STT. Outcome measures demonstrate the difference in the student’s quantity and wality of written expression. This case report increases the literature to support occupational therapy in implementing STT in the classroom to support a student with SLD in written expression to access grade-level curriculum.