A recent Jamaican school-based survey revealed that 23.1% of 13–15 year-olds, had attempted suicide one or more times during the last 12 months. Research that links adolescent pregnancy and suicidal behaviour is lacking in Jamaica. Psychological distress and suicidal behaviours amongst pregnant adolescents elsewhere in the Americas has been documented at prevalence of between 13.3%–20%. The purpose of the study was to explore the experiences and the impact of pregnancy on pregnant adolescent psychological health. Individual interviews and focus groups were conducted with adolescents in two Jamaican antenatal clinics. One clinic was designed as a ‘Teen Pregnancy Clinic’ and the other used the standard antenatal clinic design. The following themes were identified: decision-making, resilience, social support, community support system, distress, and perceptions of service. Participants reported positively on the specific interventions tailored to their needs at the Teen Clinic. Although motherhood is valued, none of the pregnancies in this study were planned by the mother. Of the 30 adolescents interviewed, seven cases were referred for counseling due to their need for emotional and psychological support. One of the adolescents reported recent sexual violence and another reported having experienced childhood sexual abuse. Historically, Jamaican adolescent mothers faced barriers to education, self determination, and family planning. Empowering, adolescent-centred healthcare and comprehensive reproductive health education may mitigate psychosocial distress.