Task persistence is related to attentional regulation and is needed for the successful transition to school. Understanding preschoolers' task persistence with caregivers could better inform the development and prevention of attention problems across this transition. Preschoolers' real-time task persistence profiles during problem-solving tasks with mothers (N=214) and fathers (N=117) were examined as antecedents of teacher-rated attention problems in kindergarten, accounting for child temperament, parenting, and preschool attention problems. Group-based trajectory modeling identified five profiles with mothers and four with fathers; more children showed high task persistence with mothers than fathers. With mothers, when persistence started low and increased over time, children had lower inhibitory control, higher verbal skills, and received more directives. This increasing profile had the highest-rated attention problems, followed by the stable low persistence profile; both groups showed higher attention problems than children who started high and declined slowly in persistence over time. Results implied children who start tasks low in persistence may require the most maternal effort to get on task, and whether those efforts are successful (increasing persistence) or not (stable low persistence), may be the same children teachers perceive as having the most attention problems. Profiles with fathers were not associated with attention problems but pointed to the importance of father-child affective processes (child negative emotion, paternal praise) in children's task persistence. Findings suggest mothers and fathers play different roles in regulatory development and that person-centered profiles of self-regulation in context may inform the prevention of children's regulatory problems. [This paper was published in "Journal of Abnormal Child Psychology" v47 n6 p947-960 2019.]