Local special education administrators (LSEAs) are integral in facilitating career development services for students with disabilities alongside their peers, particularly in rural school districts. This qualitative study explored the perceptions of 12 LSEAs regarding their contributions related to career development for students with disabilities in their southeastern U.S. rural districts and the factors they perceive to shape their own ability in this area. The emergent grounded theory indicated that LSEAs viewed their own roles in career development to vary widely and compete with other priorities as well as to be contextualized by their knowledge and awareness of opportunities within their districts and communities. Furthermore, LSEAs perceived these roles to be shaped by their collaborations within their districts, their partnerships in the community, the involvement of students’ families, and training and supports available to them. Recommendations for research, practice, and policy with respect to extending the contributions of LSEAs are provided.