Black, Indigenous, and students of color (BIPOC students) in high school, who are dually experiencing the socially constructed labels of race and disability (BIPOC-SWD), are not provided with equitable access to Career and College Pathway (CCP) programs, which contributes to a lack of preparedness and success within postsecondary settings. Despite school reform policy efforts that incorporate Culturally Relevant Pedagogy (CRP), (Gay, 2002, 2010; Ladson-Billings, 1994, 2014) and Career and College Readiness frameworks (Conley 2010; Farrington et al. 2012; Monahan et al. 2020; Morningstar et al. 2017), BIPOC-SWD perpetually have lower achievement rates, poorer postsecondary outcomes, and are less prepared for careers or college (Monahan et al., 2020; Lipscomb et al., 2017; McFarland., 2017; Newman et al., 2011; Castro, 2020). Utilizing a Disability Critical Race Theory (DisCrit) (Connor et al., 2016) lens, this comparative case study was used to examine educator perceptions of the purpose and accessibility of CCPs, barriers and supports of evidence-based practices (EBPs), and traits of students who are both successful and unsuccessful in accessing or completing CCPs in a Pacific Northwest School District. A variety of educators participated in semi-structured interviews. Findings of this study include a comparison of results based on participant role and location. Significant findings included specific practices and systems contributing to gatekeeping and pushout being heavily dependent on individual educators, unclear understandings of EBPs, and heavy emphasis on educator willingness to advocate and collaborate to support diverse learners. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]