Background/Context: High school educational environments find Black males experience systemic racial microaggressions in the form of discipline policies, academic tracking and hegemonic curriculum (Allen, Scott, & Lewis, 2013). Black males in high school are more likely than their White male peers to have high school truancies and be viewed as intentionally sinister (Allen, 2010; Osyerman, Gant, & Ager, 1995). African American males are labeled by White teachers and administrators as deviant for issues like talking in class, dress code violations and being tardy (Skiba et al., 2011). Deficit perceptions about African American students as held by White teachers and administrators serve as racial microaggressions within K-12 context. Purpose/Objective/Research Question/Focus of Study: Racial microaggressions based on prejudicial White beliefs of teachers impedes the learning process of participants. Racial microaggressive acts are problematic due to being a symptom of the overarching campus racial climate, which is often indicative of the negative historic treatment of Black males by Whites (Smith, Hung, & Franklin, 2011). The cumulative impact of racial microaggressions on Black males negatively impacts self-image, academic performance, and social navigation skills (Solórzano, Ceja, & Yosso, 2000; Steele, 1997; Steele & Aronson, 1995). Examining how Black males responded to racial microaggressions by White teachers and administrators at culturally diverse high school settings was the impetus for this study. Research Design: To understand how African American male students responded to racial microaggressions qualitative research was used. Conducting a study that focuses on multiple individualistic lived experiences, I am mindful that "human actions cannot be understood unless the meaning that humans assign to them is understood" (Marshall & Rossman, 2011, p. 53). This comparative case study allowed for narrative expression, which informed the experiential meanings participants assigned to enduring racial microaggressions by gathering in-depth information through multiple sources to understand participants' real life meanings to situations (Flyvbjerg, 2006; Merriam, 1998). Conclusions/Recommendations: Participants' engaged in pro-active navigation strategies to minimize and counter racial microaggressions. Navigation strategies were influenced by in- and out-of-class interactions with White teachers and student peers. Analysis of the data gathered during interviews, focus groups, and observations confirmed the racial microaggressive lived experiences of participants. Three themes emerged: (1) monolithic targeting; (2) integrative fluidity; and (3) behavioral vacillation. Participants avoided monolithic targeted racial microaggression(s) by creating meaningful alliances within other racialized student populations by utilizing social and extracurricular relationships as protective barriers to lessen the adverse effects of racial microaggressive experiences.