The results of a pilot program to provide transition services for high school seniors with disabilities via one-on-one mentoring services over the course of an academic year were examined. Results indicate significantly improved attitudes toward requesting accommodations over the course of the nine month program. These results suggest positive outcomes associated with the pilot program including increased application and subsequent enrollment to postsecondary education over and above national estimates. Information highlighting aspects of the program are provided including the positive preliminary results of the program. The paper concludes with a section on lessons learned and future adjustments in order to provide some practical program guidance for individuals who anticipate beginning a similar program.