Residential medical specialty camps provide short-term psychosocial benefits to youth with health conditions during summer camp, yet extinguishing effects are commonly seen in follow-up data as campers return to home and school settings (Dawson, 2017; Knapp et al., 2015; Moola et al., 2014; Plante et al., 2001). Innovative year-round support approaches are needed to enhance existing residential medical camps to improve long-term psychosocial outcomes associated with the months following the summer experience (Dawson, 2017; Dawson et al., 2018). This study is a qualitative analysis of an online mentoring support program designed as a follow-up approach in the months after residential summer camp experience has ended. The mentoring support program matched adolescent campers with a physical disability to an adult mentor having a similar disability and was structured through an online support curriculum facilitated by a recreational therapist. Qualitative analysis yielded two major themes from mentors and mentees (a) mentor as a disability life coach providing psychosocial support and expanding life expectations, and (b) barriers and facilitators to the mentee-mentor relationship. Discussion centers on insights for further developing this mentoring support program as an adjunct to traditional medical specialty camps.