Disparities in academic performance have been found in students from underserved districts. This is especially prevalent in students with disabilities. Technology use can help to narrow this divide. Mainstream software packages are readily available to most districts and increasingly include accessibility features (AF) to enable students to complete academic tasks at relatively low cost. Occupational therapy practitioners (OTPs) can support student success through the use of AF available to all students, including assistive technology (AT) for students with disabilities. Students' successful use of technology is often contingent on help from their teachers, however, teachers may need support to facilitate this process. This study describes the results of a pilot training program for teachers in an underserved school district designed to facilitate sustained use of AF that are readily available for implementation in the classroom. This paper discusses the lessons learned from provision of this training program to inform the OTP role in support of processes with similar objectives. Factors that influence teachers' perceptions of the utility and comfort with the features are reported.