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In this study, we examine the supportive and hindering factors that influenced 26 teachers’ implementation of pedagogy learned through a research-based, resource-intensive literacy PD initiative (100+ hours). Through post-intervention interviews, we explore the space between learning and enactment of new practices for literacy teaching and learning. Specifically, we ask, What are teachers’ perceptions of the contextual factors that support and hinder their moving from learning to implementation of literacy PD? Results indicate four primary supportive factors (PD facilitators, communities of practice, schools/administrators, and student affective responses) and three primary hindering factors (circumstantial factors, lack of resources, and mismatches between school or district demands). Identifying and considering these factors is an important step toward increasing implementation, which serves as a gatekeeper between teacher learning and student outcomes.