Children born with HIV in Trinidad and Tobago are surviving until adulthood, especially with free and increased access to antiretroviral therapy. As highly active antiretroviral treatment (HAART) becomes more widely available in the Caribbean, there are an increasing number of babies born with HIV who are surviving to adolescence and adulthood. HIV-positive adolescents face a number of issues shared with other adolescents who are coping with other chronic illnesses. They also face the psychosocial impacts of HIV, which is highly transmittable and still highly stigmatized. However, at present there is little or no support in place to help these children cope with issues they may face as a result of their medical condition. This single case study focuses on the issues and consequences of HIV/AIDS in the Caribbean, especially as it relates to children and teenagers born with HIV. The findings identified that the subject was well supported by her family and peer support group. The findings also suggest that the problem can only be reduced through continued public education, and policies and laws aimed at reducing stigmatization and discrimination against persons living with HIV and AIDS. The author recommends that HIV prevention strategies for women and girls, especially those of childbearing age, need to be implemented and continuously monitored and evaluated.