High school counselors support students across three areas or domains: academic, socio-emotional, and college and career development. Growing confusion and tensions around the time and responsibilities of school counselors have accompanied ever-evolving changes with their roles and coincided with continual efforts to address the K-12 and potential post-secondary educational opportunities, especially those from lower socioeconomic and particular racial and ethnic groups. The global health pandemic exacerbated challenges these student populations faced and greatly impacted the work of counselors. This qualitative multi-site case study draws on the triangulation of one-on-one interviews with twelve high school counselors across six school sites, in Southern California, with website and demographic analysis, and analytical memos, to identify institutional and personal influences on counselors' views and perspectives around education and work, and in turn, how counselors assist different student groups with their post-secondary aspirations. Findings indicate that counselors' views of education and work in light of the transition to adulthood; institutional structures and resources (e.g., distributed counseling) between charter and non-charter schools, and institutional aims (e.g., increase college going culture), and perceptions of students and communities, influence how counselors work with students and which pathways they (dis)encourage. Much of their efforts take place considering their views about students embarking on adulthood and what they feel they will be tasked with after high school. This influences the type of information they offer students, which promotes values around living meaningful, successful, and independent lives, as well as prioritizing college over career and technical education pathways. [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.]