The purpose of this longitudinal study was to examine preservice and first-year music educators' perspectives on fieldwork activities embedded within a music teacher preparation program. One cohort of students was tracked for 2.5 years as they participated in an elementary teaching practicum, fulfilled the student teaching internship, and ultimately entered the field. Drawing on data from a previous study of the same cohort's perceptions of a service-learning project (2013), this report provides a comparative analysis of the students' evolving perceptions of fieldwork over time. The perceived transfers of emergent skills and dispositions to the first year of practice also are explored with particular attention to the voices of first-year teachers. Findings suggested a wide range of benefits associated with each type of fieldwork, including overlapping and unique constructs. Perceived collective transfers included comfort and experience, habits of self-reflection, skills and knowledge for job interviews, and comfort with the observation process. These findings may assist higher education professionals as they design field-teaching activities and make informed decisions about best practices in music teacher preparation.