We examined pedagogical strategies for facilitating and developing songwriting skills with 17 males incarcerated at a U.S. medium security prison. We also investigated the participants' sense of self-worth, purpose, and social adjustment related to their participation in the songwriters' workshops. The songwriting sessions spanned over two 13-week, 60-minute workshops and one nine-week 90-minute workshop, totaling 35 weeks. Using grounded theory procedures, we analyzed four types of data: 42 sets of original lyrics, written reflections from three instructors, transcriptions of four workshop sessions, and narrative data from participants, totaling 127 single-spaced pages. Our findings indicated that the collaborative and social nature of the songwriting workshops provided a supportive atmosphere where participants generated new songs for enjoyment and expression. Participants wrote about struggles and hardships, especially relationship problems, and our data suggested that the discussions about song topics helped them cope with their incarceration. Implications for music education are discussed.