Music therapy research with youth who are grieving often reports on a combination of interventions, such as lyric analysis, improvisation, and/or songwriting. Unfortunately, the lack of theoretical transparency in how and why these interventions affect targeted outcomes limits interpretation and application of this important research. In this exploratory study, the authors evaluated the impact of an 8-session, theory-driven group songwriting program on protective factors in adolescent bereavement, and also sought to better understand adolescents' experiences of the program. Using a single-group, pretest-posttest convergent mixed methods design, participants were enrolled from three study sites and included 10 adolescents (five girls and five boys), ages 11–17 years, who self-identified as grieving a loss. Outcomes measured included grief, coping, emotional expression, self-esteem, and meaning making. Qualitative data were captured through in-session journaling and semi-structured interviews. There were no statistically significant improvements for grief, self-esteem, coping, and meaning making. Individual score trends suggested improvements in grief. The majority of the participants reported greater inhibition of emotional expression, and this was statistically significant. Thematic findings revealed that the program offered adolescents a sense of togetherness, a way to safely express grief-related emotions and experiences verbally and nonverbally, and opportunities for strengthening music and coping skills. These findings suggest that engaging in collaborative therapeutic songwriting with grieving peers may decrease levels of grief, enhance creative expression, and provide social support. More research is needed on measuring self-esteem, emotional expression, coping, and meaning making outcomes in ways that are meaningful to adolescents.