High school vice principals do not typically play a key role in the instructional leadership duties at their sites, as they are typically responsible for being their school's chief disciplinarians, managers of attendance, and supervisors of student activities and athletics. This study examined the role and responsibilities of high school vice principals in one large urban school district, for the purpose of exploring the factors that impact vice principals' abilities to participate in instructional leadership duties at their school sites. Using the qualitative tradition of phenomenology, the researcher conducted interviews with 16 participants to explore the operational and instructional leadership roles and responsibilities of senior high school vice principals in one large urban school district. The findings of this study indicated that high school vice principals in this district spent more time tending to their operational leadership responsibilities and less time on tending to their instructional leadership duties. The following factors appeared to negatively impact vice principals' instructional leadership abilities: time spent on tasks such as disciplining students and performing various operational tasks throughout the course of the school day; lack of mentoring and guidance from their principal; lack of targeted professional development to strengthen their instructional leadership skills; and a lack of administrative and instructional leadership experience. The study also identified several areas in which educators such as school districts and site principals can support the growth of vice principals as instructional leaders.