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Reverse mentoring is a means to address the social work Grand Challenge of social isolation. Among older adults, reverse mentoring can improve social connection by increasing the digital competence of older adults so they can use technology for social benefit, and by facilitating intergenerational connections with young adult mentors. In this paper, reverse mentoring is examined within an intergenerational program that serves older adults and utilizes the native technological knowledge and skills of young adults who mentor older adult participants. Qualitative data were collected through young adult mentor logs of each session, and through open-ended questions on the post-surveys collected from older adults and young adult mentors. Qualitative analysis revealed three themes related to social connection: (1) an increased sense of self-efficacy for older adults as they build confidence in technological use, and for young adults as they develop leadership skills through mentoring, (2) the breaking down of age-related stereotypes, and (3) intergenerational engagement and connection. The findings demonstrate that reverse mentoring can be used in various settings to decrease the social isolation of older adults by developing intergenerational connections and increasing older adult usage of technology.