This study investigated the changes in parents’ perception in relation to the risks associated with play before and after their children entering kindergarten. Kindergarten parents (N = 154) were asked to complete questionnaires; a factor analysis was performed on the data obtained. The results revealed that there are four key factors involved in parents’ perceptions of the risks involved in play: “dangerous evasion,” “risk management by children,” “uneasiness regarding dangerous play,” and “safety management in play.” Perceptions regarding the first three factors changed for parents after their children entered kindergarten; a certain level of risk was recognized in play activities. Watching their children participate in risky play was a major factor that influenced changes in perception according to many of the responses. In addition, for some participants, talking with the class teacher directly and/or experiencing the play area for themselves was well received, i.e., it had a greater positive effect on perceptions than letters to the parents.