Animal studies have consistently demonstrated that maternal obesity and a high-fat diet during lactation enhances obesity risk in the offspring. However, less is known about these potential obesogenic programming effects in obese humans. We propose three important pathways that may explain obesogenic programming effects of human breastmilk. First, human milk components and hormones may directly affect child eating and satiety characteristics. Second, human milk constituents can affect child microbiota that, in turn, may influence child eating and weight outcomes. Third, human milk composition may affect child eating and weight outcomes through flavor exposure. We reviewed a few very recent findings from well-powered longitudinal or experimental human research with regard to these three pathways. Moreover, we provide a research agenda for future intervention research with the overarching aim to prevent excessive pediatric weight gain during lactation and beyond. The ideas presented in this paper may represent important "black box" constructs that explain obesogenic programming effects during lactation. It should be noted, however, that given the scarcity of studies, findings should be seen as working hypotheses to further test in future research.