Grounded in role socialization theory, we examined the perceptions of teacher-coaches at an Australian independent, regional school regarding the challenges and opportunities associated with performing this dual role. This interpretivist exploratory case study was conducted with 10 teacher-coaches of various backgrounds and experience levels. Data were collected through semistructured interviews and analyzed using a data-driven reflexive thematic analysis. Three themes were identified: (a) teacher-coaches preferred teaching over coaching, and a mismatch existed between administrators’ position and teacher-coaches’ perceptions of school practice; (b) participants identified enhanced relationships with students and career enhancement as opportunities in performing the dual roles; and (c) perceived challenges included time pressures, insufficient coaching preparation, and development opportunities. Findings highlight the complexities in successfully navigating the dual role in this context. Consideration of role preferences, challenges and opportunities, and localized coaching supports may help optimize teacher-coach, student, and school outcomes.