The article considers street-connected children and their right to play. By drawing on a qualitative case study involving interviews and focus groups with NGO workers and children who lived on the streets in the Kathmandu valley, this article explores play, its role in children's lives and the applicability of the UNCRC Article 31. We argue that play forms an important part of street-connected children's lives, helping them to develop friendships and solidarity. However, in some instances play becomes ambiguous, associated with risk and crime. We propose the notion of 'ambiguous play' to explore this further. For these children, play is closely related to survival, to earning an income and engagement in crime, which can, at times, be considered a form of enjoyment or fun. This takes discussions into ambiguous areas, in stark contrast to normative notions of play associated with childhood innocence, deeply embedded within wider ideals of childhoods, rooted in coloniality. We reflect on this in light of ethical and moral dilemmas related to ambiguous play as well as implications for research, policy and practice.