The last several decades witnessed dramatic changes to US tax and transfer programs. Despite an abundance of research evaluating the effect of these work-based policy reforms on single mothers’ employment and welfare behavior, little is known about mothers’ subjective well-being. Using unique data from the DDB Worldwide Communications Life Style survey, this study examines several dimensions of single mothers’ subjective well-being before and after the full implementation of policy reforms, finding that single mothers experience large deficits in most indicators of well-being. However, over the past few decades, these mothers witnessed absolute and relative increases in global life satisfaction, declining regrets about the past, and improvements in financial satisfaction. Nearly all of these gains occurred after implementation of the tax and transfer reforms. In contrast, results from measures of self-reported stress and anxiety suggest that single mothers’ condition worsened slightly following the transition to a work-based policy regime.