Meaningful community involvement has been linked to enhancements in student achievement and quality of educational experiences. Assistant principals are positioned to build effective partnerships yet remain understudied in the leadership preparation field. This qualitative study investigated how assistant principals (N = 9) serving historically marginalized populations conceptualized and realized community leadership amidst prescriptive measures embedded within the Title I School Improvement Grant. This study highlights how the collective conceptualization of community leadership is complex and deserving of additional consideration. Findings indicate that school leaders desire more effective and sustainable partnerships, yet policies and knowledge gaps present unique challenges to change efforts.