Although a significant number of HIV-positive women intend to have children in the future, few work with providers to safely plan pregnancy. We conducted 20 semistructured in depth interviews with HIV-positive adolescent and adult women receiving HIV clinical care in an urban setting. Participants were purposively sampled to include diversity in age and childbearing plans. Interview transcripts were analyzed and coded independently by two study team members before reaching consensus on emergent themes. Among this sample of HIV-positive women (mean age = 27.9, 95% African American, 50% on antiretroviral therapy [ART], 65% want a biological child), only 25% reported discussing their childbearing goals with their HIV provider. Women actively trying to conceive recognized the risk to themselves and their partner, but had not talked with their provider about safer conception strategies. Data regarding provider communication about childbearing were organized by the following emergent themes: (1) confusion and concern on how to conceive safely, (2) provider characteristics or dynamics that influenced communication, and (3) provider guidance offered regarding childbearing. Even in this unique study setting in which referrals for preconception counseling are possible, women were unaware of this specialized service. Provider initiated reproductive counseling is needed to strategically avoid or plan pregnancy and reduce risk of transmission to partners and infants rather than leaving it to chance, which can have major health implications.