In this article, we synthesize literature related to the experiences of students with learning disabilities in postsecondary settings, including support service initiatives. We also synthesize the role of the learning strategists in context of working with these students. We then explore the daily experiences of two senior learning strategists situated in a college and university. We highlight changes in role enactment over the last decade and explore their perceptions of the factors that facilitate or hinder their role enactment as well as the resulting tensions. Finally, we highlight the differences in role enactment across the two participants and discuss the associated implications for students with learning disabilities and other service providers.