The purpose of this qualitative study was to represent the professional lives and work of four experienced music educators who teach in multiple music classroom contexts. The central question developed for this study was: How do participants describe the key elements in their professional lives and work in multiple music classroom contexts? Portraiture was the research approach, and intensity sampling was used to select participants based on the criteria of teacher experience, the diversity of their daily class schedules, and the settings in which they teach. Data sets included individual interviews, observations, photographs, and stimulated recall episodes. Data were analyzed using In Vivo coding, an inductive method that allowed me to draw directly from participants' language to create codes and themes. I created individual participant portraits which were further divided into the overarching themes of music teaching and learning in multiple music classroom contexts; school work; relationships; and navigating personal and professional life intersections. Trustworthiness was addressed through the following: (a) triangulation; (b) member checks; (c) researcher reflexivity; (d) peer review; and (e) audit trail. Findings indicated that the teaching of musical concepts across multiple music classroom contexts seemed to be almost second nature for the experienced educators in this study. When discussing curriculum and planning, participants spoke very little about music content and more about the challenges of teaching different age and ability levels throughout the school day. Participant data aligns with past literature surrounding adaptive expertise, teaching outside of specialty, micropolitics, professional development, relational and social needs, and role stress. Implications for preservice teacher education include continuing discussions about building relationships, fostering autonomy, and reaching out for help when needed. Suggestions for inservice teacher professional development and support include providing appropriate content- and context-specific opportunities for experienced educators who may need supported differently than they did earlier in their careers and providing mentoring opportunities for teachers who work in multiple music classroom contexts to balance feeling unprepared for these situations when finishing undergraduate programs that are specialized. Future research should continue to study teachers in multiple music classroom contexts with longitudinal methods, quantitative designs, and varying populations of educators. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]