Outdoor play with its risks is necessary for optimal child development. Increasing attention is being paid to factors influencing children's opportunities for risky outdoor play, with parent/guardian (hereafter parent) perceptions being an important, under-researched topic. This research explored parents' perceptions of preschoolers' risky outdoor play. Interviews were held with 19 parents of preschoolers in Nova Scotia, Canada. Bronfenbrenner's ecological model was used to consider levels of influence related to parents' perceptions of risky outdoor play. A qualitative descriptive approach identified key themes from interviews. Microsystem-level factors influencing parents' perceptions included children's age, size, ability to self-assess, and comfort with risk. Mesosystem-level factors were children's companions and supervision during play. Exosystem-level factors included neighborhood location, perceived safety, and house type. Macrosystem and chronosystem-level factors included how parents' perceptions of weather and season affected children's play, and the influences of higher societal expectations of injury avoidance on children's play over time. Findings can be used to inform strategies to promote children's quality outdoor play through understanding the factors influencing parents' perceptions of preschoolers' risky outdoor play.