Research about dual enrollment (DE) participation indicates high school students' success on various academic achievement measures including enrollment, achievement, attainment, and persistence in college. Background environmental influences, specifically staff in the high school and college settings may contribute to the positive outcomes of DE but have yet to be explored. Staff, both academic (instructors) and academic support (high school counselors and higher education institution staff, such as academic advisors and DE coordinators), support students through their DE coursework. Community colleges, in particular, provide a large percentage of DE courses and authorize and supervise DE instruction and would benefit from understanding the perspectives and work of high school counselors (HSCs) related to DE as DE expands and collaboration is needed. This qualitative study explored HSCs' perceptions and roles related to the expansion of DE offerings. Findings include HSCs' perspectives of benefits and challenges of DE, processes for identifying students for DE participation, expecting independence or fostering it through DE, commitment of counselors to promote DE success, and an individualized approach to meeting the needs of DE students. Implications for practice and recommendations for future research are discussed to inform the work of partnering high schools and colleges.