People living with HIV (PLHIV) continue to have children after being diagnosed with HIV, yet little research attention has been paid to actual lived childbearing experiences of PLHIV post-HIV diagnosis. We interviewed 10 HIV-positive women and 11 HIV-positive men in Iringa, Tanzania, about their experiences of conceiving and having children after being diagnosed with HIV. We adopted an approach to data analysis based on grounded theory and phenomenology. Participants’ experiences were shaped by social and institutional factors. Some participants reported pressures to bear children by partners and relatives, whereas others reported negative reactions from others concerning their pregnancies. Most participants had not discussed having children with a provider before attempting to conceive. Some reported being reprimanded by health providers for getting pregnant without seeking their advice. Consideration of support systems and challenges surrounding the childbearing experiences of PLHIV can help inform reproductive health interventions for those who desire children.