The purpose of this study is to highlight the experiences of teachers during the third iteration of a U.S.-based professional development (PD) program (Kennedy, 2016) for English language teachers (ELTs) in Azerbaijan and explore necessary factors when designing PD for another country or cultural/linguistic context. Designed with the conceptual framework of situated learning (Lave & Wenger, 1991), the PD program centered learning in the context of real lived experieccnces and focused on developing leaders in local communities of practice. We utilize the intrinsic case study methodology (Stake, 1995; Yin, 2003) to explore the experiences of five focal Azerbaijani ELTs during the PD program. We found that participants of the PD course are dedicated practitioners who seek opportunities to grow in their profession; the PD course strengthened their communities of practice, growing confidence among teachers in speaking English; and it promoted limited pedagogical learning and applications in the classroom. However, teachers faced environmental and policy challenges that largely hindered changes to their teaching practices. This study points to implications for future PD programs designed for cross-cultural contexts by building on Desimone’s (2009) framework for effective PD by adding core features and essential contextual factors that must be considered.