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Continuation high schools serve students for multiple reasons. Among them are low credit attainment, excessive absences, probation status, and discipline problems. Students in these programs often have many educational gaps. In the state of California, continuation high schools have been an educational option for this vulnerable student population since 1919. This segment of the school system seeks to offer students with diverse educational challenges and obstacles a second opportunity to complete their education. Presently, there is little research connected to the success of continuation high school graduates’ level of persistence in any type of higher education. This study examined the influence teacher-student relationships had on a particular group of continuation high school students who, in spite of challenges associated with continuation-education deficit mindset, were able to attain academic success in higher education. The study sought to explore how the practices of comprehensive high school sites intersected with those of a specific continuation high school. Social Capital and Critical Race Theory provided the conceptual lens to analyze teacher–student relationships. The researcher captured students’ and teachers’ perceptions in order to analyze how their interactions and relationships could be strengthened to ensure student academic success and provide continuation high school students with options upon high school graduation.