With digital media use on the rise among adolescents and adults alike, youth-serving organizations, and mentoring programs in particular, are increasingly in the position of having to develop policies that take advantage of the potential benefits of social media use, while guarding against potential risks. However, little data exists on program policies or use of various forms of digital communication (i.e., texting, email, Facebook, Skype, photo sharing) in the context of youth mentoring relationships. There is also a lack of research on the perceived impact of digital communication on the quality of mentoring relationships. Drawing on cross-sectional data from 258 mentors and 147 mentoring program staff primarily from the United States and Canada, this study examined how digital media is used in formal mentoring programs and investigates associations between digital media use and mentoring relationship characteristics, as well as staff and mentor perceptions of the influence of digital media use on the mentoring process. Results indicated that although digital media is being used, particularly in relationships with older mentees, there is substantial variation in program policies around its use. In addition, the impact of digital media use on mentoring relationship quality and duration was generally perceived by mentors and staff to be neutral or positive, and use of digital media between mentors and mentees was associated with greater relationship quality and duration. Implications for mentoring program practice and future research are discussed.