This study describes a Head Start teacher professional development program conducted by a well-respected theatre-in-education organization. The professional development program provided teachers with opportunities to observe and participate in classroom drama sessions, introduced them to drama strategies and techniques, and guided them through a step-by-step process so they could immediately apply what they learned. This research details the benefits and difficulties of implementing this type of program, elucidates ways education directors and teachers can contribute to or impede the success of this type of programming, and enumerates factors that should be considered before investing in teacher professional development initiatives. (author abstract)