Occupational therapy practitioners (OTPs) support teachers in the utilization of assistive technology for their students. In 2019, teachers in an underserved school district in western New York participated in a training designed to support the use of accessibility features of Microsoft Office 365 and Windows 10. The purpose of this study was to examine the long-term effects of this assistive technology (AT) training for teachers who were trained, comparing the usage of features, perceived value, perceived ease of use, and accessibility features used with students with disabilities between those who participated in the prior training with those who did not. This study used a quasi-experimental design that compared teachers in the school district who were trained on the accessibility features of Microsoft Office 365 and Windows 10 in 2019. This was measured using an online survey offered to all teaching staff in the district to compare those who did or did not participate in the training. Independent t-tests and chi-square analyses were used to compare those who did and did not receive training. Overall, the results indicated that the training had a positive impact on the usage of trained technology features. Those who participated in the training reported an overall positive impact on perceived value and ease of use, as well as implementation of trained features. OT supports students who struggle with access to learning in the classroom. AT can be an important tool to support student success. Supporting teacher use of these AT tools can help ensure continued student access to these tools in the classroom.