Highlights• Youth environmental risk was negatively associated with mentoring relationship quality.• Youth individual risk was not associated with mentoring relationship quality.• Mentors' program experience was positively related to mentoring relationship quality.• Mentors' program experience buffered the link between environmental risk and relationship quality.Abstract Because program experiences are more amendable than mentor or mentee characteristics, they may be important factors to consider in buffering the negative impact of youth risk on the quality of the mentor-mentee bond. Data from 455 mentees (ages 11-18; 57% male) and their undergraduate student mentors (82.3% female) from the Campus Connections mentoring program were used to assess whether youth risk and mentors' program experiences (i.e., program structure, supportive relationships with staff, opportunities for skill building, support for efficacy and mattering, and opportunities to belong) were associated with mentoring relationship quality and whether mentors' experience within the program moderated the association between youth risk and mentoring relationship quality. Results indicated that environmental, but not individual, risk was negatively associated with relationship quality. Mentors' experiences with the program were positively associated with mentoring relationship quality, and in many cases, above and beyond youth level of risk. Finally, mentors' perception of program structure, supportive relationships, and opportunities for skill building attenuated the negative relationship between environmental, but not individual, risk and relationship quality. Mentors' experiences of program support for efficacy and mattering and opportunities to belong were not significant moderators in any model. Implications for programs and future research directions are presented.