This collective case study examined the perceived impact of a context-specific professional development program, the Urban Music Education Institute, on urban music educators' professional growth. The year-long program, which focused on culturally responsive pedagogy (CRP), featured workshops presented by nationally recognized clinicians complemented by a collaborative teacher study group (CTSG). Portraits of individual educators' growth trajectories illuminate the multifaceted and idiosyncratic nature of teachers' professional growth. Teacher profiles further illustrate complexities inherent in the nonlinear process of learning to practice CRP. Cross-case themes included teachers' desire for "permission" to teach in contextually specific ways, sociopolitical dimensions of urban teaching as a focus for professional learning, and ways that cultural Whiteness influenced participants' processes of learning to practice CRP. The CTSG emerged as a key element contributing toward the program's context specificity. Participants used this group as a site for negotiating tensions associated with culturally responsive and socially just teaching in the company of colleagues with shared understanding of urban contexts. Implications for professional development aligned with urban music educators' discipline- and context-specific learning needs are discussed based on the findings.