Child chronic pain is both common and consequential and identification of malleable risk factors is a critical step towards developing effective interventions. Existing evidence points to the possibility that parent behavior may play a significant role in the development of children’s chronic pain through modeling of pain-related behaviors. An important parental trait that predicts parent behavior in pain contexts is parental pain catastrophizing, which has been linked to child pain outcomes as well as to increased facial pain behavior in both parents and their children during pain induction. Existing research has examined facial pain behavior in aggregate, summarizing facial expressions over the course of an entire dyadic interaction, which does not allow for evaluation of the dynamic interplay between a parent and child. The current study aimed to test the hypothesis that higher parental catastrophizing would predict decreased flexibility in emotional dynamics between parent and child (reflected in facial affect during a parent-child interaction that occurs within the context of child pain-induction), which would in turn predict fewer child chronic pain symptoms. The approach used dynamic systems analysis of facial behaviors during the parent-child interaction during the child’s performance of a pain inducing cold pressor task to assess dyadic emotional flexibility. Nine-year old children from a larger sample of twins (N = 30) were video recorded during a cold-water pain task while their parents observed them. Videos of the children and their parent from these interactions were analyzed using facial action unit software (AffDex), into positive, neutral, and negative facial emotional expressions. Synchronized parent and child coded facial data were then analyzed for flexibility using GridWare (version 1.1). Parents completed the Pain Catastrophizing Scale (PCS) to assess parental trait pain catastrophizing and the Body Pain Location/Frequency scale to assess child chronic pain symptoms during the prior three months. Contrary to prediction, parental catastrophizing was related to higher levels of flexibility, and flexibility was unrelated to child chronic pain. Exploratory analyses indicated that children with higher levels of effortful control had more emotionally flexible interactions with their parent during the cold pressor, and emotionally flexible interactions predicting lower levels of children’s negative emotional responses to the acute pain task. suggesting some promising avenues for future research.