Play is a fundamental aspect of developmental growth, yet many parents encounter significant challenges in fulfilling their caregiving roles in this area. As online content increasingly serves as the primary source of parental guidance, this study investigates the difficulties parents face related to play and evaluates the limitations of current online content. We identified ten findings through in-depth interviews with nine parents who reported struggles in engaging with their children during play. Based on these findings, we discuss the major limitations of online play content and suggest how they can be improved. These recommendations include minimizing parental anxiety, accommodating diverse play scenarios, providing credible and personalized information, encouraging creativity, and delivering the same content in multiple formats.