Twenty-five father-son dyads completed semistructured interviews designed to elicit specific preferences for teaching and learning about consistent and correct condom use and strategies for addressing common condom use errors and problems. For analysis, we used in vivo coding and vertical and horizontal analysis techniques. Fathers and sons agreed that communication about condom use is feasible and acceptable. However, fathers tended to convey vague messages regarding protecting oneself from the negative consequences of sexual activity. Furthermore, both fathers and sons reported barriers hindering conversations. Secondly, the style and frequency of condom use conversations can help overcome barriers and support father-son relationship management. Talking frequently in 1-on-1 settings and using strategies to reduce discomfort made communication easier. Lastly, fathers and sons reported distinct preferences for teaching and learning about condom use. Sons wanted fathers to give specific guidance on the use and management of condoms. Fathers expressed interest in opportunities for improving their own condom knowledge and skills. Fathers identified gaps in their own condom use knowledge as a limitation to effective instruction of their sons. A father-focused communication intervention about condom use is feasible and acceptable. Enhancing the intergenerational benefits of father-son communication by addressing specific father-son preferences and learning needs for condom use instruction, as well as communication barriers, represents a novel mechanism for reducing male sexual reproductive health disparities.