Extant research, though limited in quantity, increasingly demonstrates the critical connection between quality preparation experience, candidates' leadership capacity, and their subsequent instructional and transformation leadership practices. Using mixed methods, this study builds on the current knowledge base and aims to further verify the link between program preparation and participant learning by examining the various program features and their effect on participant learning as measured by both candidates' self-reported preparedness in key leadership areas and their objective performance from NASSP's Assessment Center. Descriptive analyses indicated that the program in question was comparable to many exemplary preparation programs in terms of participants' perception in curriculum content quality and self-reported preparedness in key leadership areas. Correlation analyses resulted in a consistent positive relationship between cohort structure and participants' self-reported preparedness. NASSP's Assessment Center demonstrated less optimistic results in candidates' leadership skills. However, this did not seem to impact participants' overall positive experience with the program. Qualitative data, while confirming many of the exemplary features of the program (e.g., cohort, mentoring and coaching) demonstrated that quick and episodic changes that characterize many urban school districts seemed to exert a great influence on the consistent implementation of the program, in particular, in internship placement, one of the most important learning blocks in the studied program. The study calls for more systematic support from the district and more seamless collaborations among the partners. (Contains 3 tables.)