A growing trend across the nation, academic coaching is a popular way for schools to embed professional development within the regular school day. This article presents the findings of a yearlong qualitative case study of a rural school academic coach and her attempts to gain entry to teachers' classrooms to observe and guide their instructional practices. Gaining entry, a vital first step, influences a coach's ability to positively affect student achievement. The findings with regard to insider status, coach identity, trust, staff connections, and teacher resistance provide implications for practitioners and researchers.