The importance of parental engagement, particularly for preschoolers, is incontrovertible. Many research studies have found that parental engagement is an important predictor of children’s academic and social development at all points of the socioeconomic spectrum. However, little is known about the obstacles to parent engagement—particularly from the first-person perspective of low-income parents. This qualitative study explores parental engagement within early education and the obstacles that lower-income parents face in achieving engagement with their children. The study involved semi-structured interviews (N = 9) of preschool parents from Philadelphia, Chicago, New York City, and Oakland. I found that all parents in this sample described themselves as highly motivated to engage with their children and confident in their ability to do so. However, parents noted that a variety of external obstacles makes this difficult. Specifically, parents identified neighborhood violence, job and personal life conflicts, outside influences on children like other children and caretakers, and lack of affordable activities in their community. In order to address these, parents talked about personal solutions (e.g., planning their time with their children) and also structural solutions (e.g., opportunities to engage that work for parents' schedules). These results demonstrate lower-income parents have less known obstacles and that issues beyond internal motivation are the true obstacles to parental engagement.