Framed in the critical race theory of structuration (CRTS), this sequential explanatory mixed methods study seeks to identify the socialization practices by examining the realities of practices of assistant principals and the ways in which they impact the disciplinary actions of assistant principals at middle and high schools. The mixed methods design was used to explore and understand: (1) the realities of practice within the school organization; (2) the socialization processes of assistant principals within the realities of practice; and (3) the ways in which those socialization processes influence their disciplinary practices. Fifty-one percent of the assistant principals invited to participate in this study completed the online survey. The survey responses led to a focused sample and in-depth interviews with three Black female assistant principals supervised by White male principals. The data from both portions of this study revealed that the structure of the realities of practice and the dimensions of the CRTS coexist and correlate within the school organization. This combination creates a Socialization Paradox Cloud that dictates assistant principals' unwillingness and/or inability to change policy adversely affecting students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]