This article reviews social work challenges in treatment engagement of men who have sex with men (MSM) and details issues co-morbidity creates for reaching HIV-positive MSM engaged in substance abuse. The literature reviewed within the article identifies HIV and substance use risk factors influencing out of care dynamics and examines relevant research identifying contextual and cultural factors central to achieving cultural competence. The article examines aspects of cultural sensitivity and competence in service development and engagement and identifies service qualities and characteristics social workers can incorporate into practice and programs to increase the likelihood of successful engagement and treatment adherence.