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Research has established that one of the most important functions assistant principals can learn is how to be an instructional leader. Some school districts have incorporated problem-based learning (PBL) in their building-level principal preparation programs for assistant principals. This study examined one approach to PBL, the Problem of Practice (PoP) project embedded in the new Level II Certification Program of a central Florida school district through a case study of six assistant principals’ experiences and perspectives based on interview, meeting observations and artifact data. The study revealed major challenges associated with implementation of the PoP projects and found that collaboration with the Level II committee was critical for their completion. The study also identified that the integration of the PoP project into the School Improvement Plan seems to be key to the success of the PoP projects. The recommendations based on these findings are made to district leaders as they continue to improve the PoP project as a central feature of the Level II Certification Program. Keywords: problem-based learning; assistant principal training