This qualitative study focuses on the intersectionality of race and rurality by looking at the responses of Wyoming principals and superintendents to the issues of diversity and social justice within Wyoming. The responses are presented and analyzed through a new framework called Cowboy Epistemology, and the Cultural Competency Continuum (Lindsey et al., 2009). It appears that despite double-digit increases in diversity between 2010 and 2018, some Wyoming school and district administrators continue to demonstrate actions and practices congruent with the demographic divide, cultural homophily, and Whiteness along with cultural worldviews that suggest a failure to: (1) value diversity; (2) engage political organizations and individuals in a manner that advocates for the needs of diverse students; (3) implement multicultural instruction beyond superficial means; and (4) engage the community in tolerance for others who are different from the traditional White Wyoming ranching, conservative, materials extraction, isolationist way of life. While outliers and standards for social justice and diversity exist in Wyoming among and for administrators, more needs to be done to prepare and train administrators to engage in culturally proficient and sustaining instructional leadership so that administrators can serve all students, engage in community leadership, and resist the negative influences of Cowboy Epistemology, demographic divide, cultural homophily, and Whiteness. Chief among the more needs to be done for Wyoming administrators is the adoption of culturally responsive school and culturally sustaining instructional leadership practices and training on the culturally proficient continuum.