The underrepresentation of administrators of color in higher education is one of the most important ethical dilemmas facing colleges and universities today. Arguably, in no place is this more evident than at historically white colleges and universities (majority institutions). Prior to the 1960s, the lack of administrators of color in higher education's Predominantly White Institutions (PWIs) was viewed as common place and a cultural normative due to the existence of segregation and widespread racism during that era. It was not until the American Civil Rights Movement that higher education was forced to expand, at which point, state and federal civil rights mandates--prompted by social justice concerns--began to challenge institutions that excluded minorities (Chang, 2005). Many of these mandates became known as affirmative action policies. Mostly race-sensitive in nature, these affirmative action policies aimed to increase access and opportunities for promotions, salary increases, and career advancement for minority employees. However, not all PWIs immediately welcomed the demand for a culturally diverse leadership upon their campuses (Arthur & Shapiro, 1995; Kawewe, 1997; Payne, 2004; Perna, Gerald, Baum, & Milem, 2007; Wilson, 1995). Studies on university hiring practices revealed that in many instances, once a minority hiring goal was met, departments stopped seeking minority applicants. In some cases, institutions took direct and intentional action to cease the recruitment of minorities (e.g., by pulling their ads from minority publications) regardless of the number of vacancies that occurred from then on (Wilson, 1995). Meanwhile, over time, legal disputes to affirmative action programs began to expose flaws amidst the policy's good intentions. Over 40 years after the American Civil Rights Movement, many of today's college and university policy makers have shown a willingness to embrace racial diversity. However, efforts to do so have proven that positioning a diverse administrative leadership to reflect the values, issues, and concerns on campus is a multidimensional and complex task (Cabrera, Nora, Terenzini, Pascarella, & Hagedorn, 1999; Holmes, Ebbers, Robinson, & Mugenda, 2000; Jackson, 2004; Jackson & Rosas, 1999; Watson, Terrell, Wright, Bonner, Cuyjet, Gold, Rudy, & Person, 2002). The purpose of this article is to summarize scholarship on the challenges of increasing administrative representation for people of color in higher education and to address implications for policy and practice.