School social workers approach their direct practice from ecological systems and justice-oriented perspectives. As such, they may hold a critical role in providing needed sexual health and dating education and services to adolescents with disabilities. Thirteen high school social workers who work closely with adolescents with disabilities were interviewed to identify their needs and challenges in supporting such adolescents toward dating and sexual health. Mesosystemic challenges at the school level evidenced three themes: (1) the desire for school-based comprehensive sexual education for all adolescents, (2) a multitiered and ancillary approach to educating adolescents with disabilities about dating and sexual health, and (3) increased time (that is, via additional funding) to provide social work services to adolescents with disabilities. Exosystemic needs and challenges were reflected in discussions about community resources that social workers deemed integral to their work with adolescents with disabilities. Finally, dialogue reflective of macrosystemic needs and challenges included environmental factors that adolescents with disabilities brought with them to school and that affected social workers' intervention efforts. Consistent with social workers' dialogue, recommendations for social work education, policy reform, and programs for adolescents with disabilities are presented.