The purpose of this study was to examine the occupational identity development of undergraduate music education majors as they participated in a yearlong authentic context learning (ACL) experience situated within a professional development school (PDS). Five undergraduate music education majors enrolled in either a string pedagogy class or an instrumental methods class were required to teach in the band or string projects at the PDS. The authors utilized a multiple case study method and collected data from interviews, observations, and participant written reflections. The transformation of data included transcribing interviews and indexing student reflections. The authors identified four emergent themes: the development of general pedagogical knowledge, knowledge of self, performer/teacher symbiotic outcomes, and professional perspectives. The impact of the perceived positive or negative ACL experiences as well as interactions with peers was mediated by either adaptive or maladaptive participant responses to ACL experiences. Participants' descriptions fit the framework of an extended apprenticeship of what the authors labeled a critical apprenticeship of observation. Based on these findings, they developed a conceptual diagram in order to describe the impact of the ACL experiences on teacher occupational identity development. (Contains 1 table and 1 figure.)