Starting a career in music education is difficult; there are many challenges that first-year band directors face. These challenges can include praxis shock, isolation, stress, and high workloads. First-year band directors may need mentoring support as they transition into the profession. There are different types of mentor programs that a school or district can provide, and many do so. Researchers have examined different mentorship models that work with varying degrees of success. In this study, I utilized a multiple case study approach to better understand the first-year mentorship experiences of three second-year band directors during their first year of teaching. Data in the form of paper artifacts from mentorship experiences and semi-structured interviews were collected using the Zoom platform. Findings included (a) difficulties with participants' mentors and mentorship programs, (b) searching for mentorship, (c) feedback and desires for mentorship programs and (d) challenges of the first year. Based on these findings, suggestions for administrators and teachers to improve the mentorship process are discussed.