Drowning is a leading cause of child mortality globally. Strategies that have been suggested to reduce pediatric drowning risk include increased parental awareness of children’s swimming ability and drowning risk, improved adult supervision of child swimmers, and providing swim lessons to children. This study explored how parents’ beliefs relevant to children’s drowning risk, perception of children’s swimming ability, and judgments of supervision needs changed as children aged two through 5 years accumulated experience in swim lessons, and compared a parent group who received regular, detailed feedback about their child’s swim skills with one that did not. Parents completed questionnaire measures near the beginning and end of a series of 10 weekly swim lessons. Results revealed that parental accuracy in judging children’s swimming abilities remained relatively poor even though it improved from the beginning to the end of the swim lessons. Supervision needs were underestimated and did not vary with program or change over the course of swim lessons. Children’s ability to keep themselves from drowning was overestimated and did not change over lessons or vary with program; parents believed that children could save themselves from drowning by the age of 6.21 years. Parents who had experienced a close call for drowning showed greater awareness of children’s drowning risk and endorsed more watchful and proximal supervision. Results suggest that expanding learn-to-swim programs to include a parent-focused component that provides detailed tracking of swim skills and delivers messaging targeting perceptions of children’s drowning risk and supervision needs may serve to maximize the drowning protection afforded by these programs. Delivering messaging in the form of ‘close-call’ drowning stories may prove especially effective to impact parents’ supervision practices in drowning risk situations.