This article investigates a yearlong professional development experience provided to two cohorts within a doctoral program for early career school leaders. Drawing from situated learning theory, we examined one aspect of this program's pedagogy, which centers on the use of field-based application-oriented projects that leaders must take up in their school settings. From this investigation, we identified and reported two key elements of the school context that were regularly drawn into leaders' application-oriented learning experiences. We also illustratively highlight several of the authentic leadership consideration and practice experiences that were enabled.