Parental alcohol dependence is a significant risk factor for harsh caregiving behaviors; however, it is unknown whether and how harsh caregiving changes over time and across parenting contexts for alcohol-dependent mothers. Furthermore, to our knowledge, no studies have examined whether and how distinct dimensions of child characteristics, such as negative emotionality modulate harsh caregiving among alcohol-dependent mothers. Guided by parenting process models, the present study examined how two distinct domains of children's negative emotionality—fear and frustration—moderate the association between maternal alcohol dependence and maternal harshness across discipline and free-play contexts. A high-risk sample of 201 mothers and their two-year-old children were studied over a one-year period. Results from latent difference score analyses indicated that harsh parenting among alcohol-dependent mothers increased over time in the more stressful discipline context, but not in the parent–child play context. This effect was maintained even after controlling for other parenting risk factors, including other forms of maternal psychopathology. Furthermore, this increase in harsh parenting was specific to alcohol-dependent mothers whose children were displaying high levels of anger and frustration. Findings provide support for specificity in conceptualizations of child negative emotionality and parenting contexts as potential determinants of maladaptive caregiving among alcohol-dependent mothers.