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This study examined a year-long, U.S. state education agency (SEA) sponsored professional development (PD) experience aimed at experienced assistant principals (APs) who were poised to soon become principals. Drawing on theories related to learning transfer and powerful learning experiences (PLEs), we were particularly interested in how participants discussed applying their learnings in the near-term as APs and in the future as potential principals. Findings suggest participants engaged in different kinds of learning transfer and that PLEs helped facilitate such transfer. On the other hand, we also found that organizational and contextual considerations, such as participants’ current principals and/or school cultures, inhibited participants’ ability to transfer their learning. We close with implications for practice and future research.