The purpose of this study was to explore how an intergenerational group of music students (ages 16-71) mentored each other in an online jazz improvisation course. This study is framed in Dewey's notion of students sharing their knowledge and experiences with the teacher as facilitator and the following research questions guided this investigation: How did the participants engage in peer mentoring? What knowledge and experiences did they share with each other? Data collection occurred during one semester of instruction and included class observations and individual participant interviews. Two themes developed during data analysis: navigating hierarchy by age and confronting difficulties in providing feedback. Findings indicated that peer mentoring was complex and multi-faceted and contributed towards redefining the notion of how peer mentoring can include students of different generations. Implications include how music teachers can use peer mentoring with students of different age groups to enhance knowledge and elevate performance skills.