The emotion socialization behaviors that caregivers engage in with their own children are influenced, in part, by their own emotional responses to situations. One theory of why caregivers' behaviors differ in response to different child emotions centers on variability in caregiver discomfort around these emotions. Further, this discomfort is postulated to stem from a caregivers' experience during their emotional expressions in childhood with their own caregivers (hereinafter called "remembered" caregiving). However, limited research exists on the interplay between caregivers' remembered caregiving experiences and their own discomfort in response to children's emotions. This study aimed to explore (a) the association between valence of children's emotions and caregiver discomfort, (b) differences across discrete emotions and caregiver discomfort, and (c) the potential influence of recalled emotion socialization experiences on caregiver discomfort. In a sample of 234 caregivers (136 mothers; 98 fathers; Mage = 35.62, SD = 4.14 years) of 146 preschool-aged children, child negative emotions were found to elicit more discomfort than positive emotions, but no emotion-level differences emerged within discrete negative emotions (i.e., anger, fear, and sadness). Caregivers who recalled that their own caregivers responded to their emotions in childhood with an outcome-oriented goal (e.g., walking away to stop the emotional display) reported more discomfort with their own children's negative emotions. These findings contribute to our understanding of intergenerational transmission of caregiving behaviors, emphasizing the role of negative caregiving experiences in shaping caregiver comfortability with their child's negative emotions. (PsycInfo Database Record (c) 2025 APA, all rights reserved).