The current study is aimed at evaluating the relationship between attachment and identity development, and their influence on psychological well-being in adolescents with and without disabilities in Kenya. The sample was composed of 296 adolescents (151 with disabilities and 145 without any disability). The mean age in our sample was 16.84 years (SD = 1.75). Adolescents with disabilities had significantly lower scores in identity formation, paternal attachment, and life satisfaction. A path model indicated that identity formation partially mediated the relationship between secure attachment and psychological well-being. Our findings indicate that both parent and peer attachment play an important role in the identity formation and psychological well-being of adolescents in Kenya, irrespective of a disabling condition. A multigroup analysis indicated that while the structure of the relationship between variables held for groups, the pattern and strength of the relationships differed. Implications for practice, especially the guidance and counseling services in schools, are discussed.