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This study examines the well-being of Japanese children in single-mother families relative to their counterparts living with both parents. Using data from the 2011 and 2012 rounds of the National Survey of Households with Children, I begin by demonstrating that single mothers report that their children have significantly worse health and lower academic performance relative to married mothers. This relationship is particularly pronounced for lone mothers (and their children). I then estimate a series of regression models to assess the extent to which the lower levels of well-being among children of single mothers’ reflect mothers’ (a) economic disadvantage, (b) difficult work circumstances, and (c) worse health and experience of stressful life events. Results indicate that economic disadvantage is particularly important for understanding lower levels of well-being among the children of single mothers, especially those who are coresiding with grandparents. I conclude by discussing the potential implications of these results for understanding linkages between family behavior and inequality in Japan and for the intergenerational transmission of disadvantage via single parenthood.