Abstract: Research shows that mentoring is a way to enhance learning and personal growth. In C.A.M.P. Osprey at the University of North Florida, college students serve as leadership mentors to K-12 students in Texas, Georgia, North Carolina and Massachusetts. To overcome geographic and financial barriers faced by high-poverty urban and rural partner schools, the program harnesses virtual mentoring through videoconferencing technology to connect K-12 students with their collegiate mentors. Cognitive apprenticeship and self-determination theory provided the theoretical frameworks for the design of the mentoring program. The mentored students demonstrated substantial improvements in GPA and attendance during their mentoring semester, with the virtually mentored students gaining as much or more than their face-to-face mentored counterparts. This paper will share successes and challenges associated with program development, implementation and technology adaptation along with previous outcomes associated with collegiate mentor and K12 mentee participants.