The term glass ceiling refers to existing artificial barriers to entry into leadership positions (Wilson, 2014, Booth, 2007). The quest for equity and social justice in educational leadership positions by racialized women, defined in this study as non-white, non-First Nations women, is the focus of this comparative case study. The key source of information for this qualitative research was the lived experiences of 12 racialized female educational stakeholders in Southern Ontario. Their experiences with the invisible barriers that prevented them from feeling included and attaining leadership positions is central to understanding how they coped with these artificial barriers to their professional advancement and how they navigated the implicit concepts organizations have created about who the ideal leader is and how they look (Pinnington & Sandberg, 2013). There have been idealized criteria in the Ontario reality about who becomes a leader at a school and who is promoted into vice-principalship, principalship, or other administrative positions by school boards. The punctuated equilibrium policy event that was the catalyst for those aspiring racialized female education leaders to have more opportunities for professional advancement in education was the pronouncements of the Ontario Human Rights Commission (OHRC) in 2012. Those pronouncements for equity and social justice in the selection of educational leaders was based on a Human Rights violation application filed by a Vice-Principal against her school board due to several years of being passed over for promotion into principalship position. This human rights violation application led to the creation of a promotion procedure for Vice-Principals and Principals in Ontario schools in 2013. The researcher divided the twelve racialized women, who volunteered to tell the stories about their lived experiences with the Ontario education leadership glass ceiling, into three cohorts according to the time period that they pursued educational leadership positions. The three cohorts comprised of four racialized women each were as follows: (1) Pre-Punctuated Equilibrium Cohort, comprised of both retired and active Principals and Vice-Principals from the pre-2013 time period. (2) Straddling Punctuated Equilibrium Cohort, comprised of classroom and non-administrative teachers in leadership roles from the 2013 2015 time period. (3) Post-Punctuated Equilibrium Cohort, comprised of newer classroom teachers with a maximum professional experience of five years after 2015. The researcher found that although the formal recruitment process is now more transparent and legally monitored in Ontario, the invisible barriers which were historically in place to prevent racialized female education stakeholders from feeling included and considered for leadership positions in educational settings are still present. This finding confirms the perspectives of Crenshaw (1989) that legal protections do not quickly change the cultural practices of organizations. The researcher also found that feelings of loneliness on the part of these racialized women was based on the lack of support from their leaders and the fact that they have to prove themselves above and beyond what is normally required of their dominant culture research informants possess more additional qualifications than their dominant culture peers, or promotion into leadership positions. However, some are still on the path to acquiring these additional qualifications because they believe these will at least give them an opportunity at being considered for the interview process. They all stress the need for sponsors who are able and willing to share their cultural capital (Bourdieu, 1986) with them to make the playing field more equal in order to make up for lost leadership time caused by decades of discriminatory practices in Ontario school leadership selections. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]