With the growth of dual enrollment in high schools, there is an opportunity to augment and enhance college acceleration opportunities for historically underrepresented students seeking post-secondary matriculation. In 2016, California enacted progressive legislation through Assembly Bill 288, which specifically identified the need to increase college and career readiness for underrepresented students through dual enrollment. The literature on equitable participation and outcomes is limited due to the sudden growth and access to dual enrollment in California. As a result, research is limited and does not reflect current complexities involved in equitable participation and outcomes for historically underrepresented students. The purpose of this qualitative case study was to explore dual enrollment through the perceptions, attitudes, and experiences of Hillside School District (HSD) and City College educators involved in dual-enrollment programs. This case study captured the experiences of seven participants through semi-structured interviews. In addition, a document analysis was conducted to explore the impact of student pre-enrollment tasks and processes mandated by HSD and City College officials. The key results of this dissertation study uncovered a need for institutional reforms such as additional high school counselors, enhanced targeted outreach and strategic recruitment to attract underrepresented students, changes to the cumbersome application and registration process for students, creating district and school committees to create action plans, and improvements for the onboarding of dually enrolled 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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]