Objective: Parenting interventions have demonstrated some potential for effectiveness in improving psychosocial and health outcomes for children with type 1 diabetes (T1D) and their families. However, most interventions have been tested with parents of adolescents, and engagement of parents of younger children into parenting interventions remains problematic. This study aimed to assess the feasibility and acceptability of the Positive Parenting for Healthy Living program for parents of children with T1D. Methods: We describe our experiences with engagement and recruitment of parents of 2- to 10-year-old children with T1D into a randomised controlled trial of a brief parenting intervention. Engagement, including rates of enrolment, assessment completion and session participation, as well as feasibility were assessed at multiple time points during the trial using multiple measures. Results: We share our learnings in delivering and evaluating a parenting intervention for this population. In particular, we explore reasons for the low rate of enrolment, parents’ resistance in opening up about their problems, possible discrepancies between parent and practitioner views on the nature and extent of emotional and behavioural problems, and how better to target engagement efforts in the future. Conclusions: We offer recommendations for engaging parents in future trials and parenting intervention initiatives.