Prompt entry into care and retention in care are critical for improving outcomes among HIV-infected individuals. This study identified factors associated with HIV-infected adolescents who delayed entry into HIV care (DEC) after diagnosis of HIV or who fail to remain in care afterward (FRC). We reviewed clinical, demographic, and social data from the records of 202 HIV-positive adolescents (13-21 years old) infected via high-risk behaviors. Strength of association between clinical and social factors and DEC or FRC were estimated with log-linear regression models. DEC occurred in 38% (76/202) of adolescents. Factors independently associated with DEC were unstable residence (RR 1.5; CI: 1.0-2.1) and, compared with less education, college attendance (RR 2.1; CI: 1.5-3.2). FRC occurred in 29% (52/177) of adolescents established in care. Compared with college attendees, high school students (RR: 4.5; CI: 1.2-17.3) and those who dropped out of high school (RR: 4.0; CI: 1.1-15) were more likely to FRC. Compared with adolescents with private insurance, adolescents without insurance (despite access to free care) were more likely to FRC (RR: 2.8; CI: 1.1-6.9). Controlling for sex, adolescents with children were more likely to FRC (RR: 1.8; CI: 1.0-3.1). Interventions to avoid DEC that target HIV-infected adolescents with unstable residences or those diagnosed while attending college are warranted. Among patients engaged in care, those with only high school education or without insurance-which may be markers for socioeconomic status-need additional attention to keep them in care.