This article presents findings from a qualitative case study of a 9-week collaborative early childhood drama education program. It focuses on collaborations between a drama specialist and two early childhood classroom teachers at a private school in the Midwestern United States. A full-time drama specialist with educational background and professional experience in drama and two experienced early childhood teachers were the main participants. Analysis illustrates the participant teachers' roles, expectations, and interactions with each other. The results identify specific aspects that hindered the collaborative process at the individual teacher level (unclearly defined leadership, the lack of communication, and perceptions of insider versus outsider) and at the institutional level (the absence of school regulations and support). Suggestions including structured school-wide support and incentives in addition to individual teachers' efforts for a successful collaboration are provided. (author abstract)