Ugandan adolescent girls and young women are disproportionately impacted by human immunodeficiency virus, and this is largely driven by their engagement in transactional sex. Globally, parent–daughter communication about sex is associated with increased contraceptive use and delayed/decreased sexual activity, but research on parent–daughter communication about transactional sex is lacking. This paper elucidates local perspectives on, and experiences of parent–daughter communication about sex and transactional sex, to inform family-level comprehensive sexuality education interventions. It is based on research with adolescent girls and young women aged 14+, and men and women in Kampala and Masaka between 2014 and 2015. We suggest that family-level comprehensive sexuality education interventions targeting parent–daughter communication about sex could further highlight the role that fathers might play, and emphasize communication about the inequitable power dynamics in transactional sex and condom negotiation skills, while reducing fear surrounding parent–daughter communication.