This research focuses on parental experiences of trustful collaboration with teachers and school personnel in Finnish schools when they have children needing support. According to previous research, the relationship between schools and parents when a child needs support is usually seen as a subject of continuous negotiation. Parents often have limited influence, while experts, such as teachers, leverage their authority and status in decision-making processes related to supporting children. The parent’s position seems to be questioned; as such, their position as an influential authority is vulnerable. Based on interview data, this study qualitatively examines how parents experience trust, or the lack thereof, towards their child’s teachers. The phenomenographic result, “outcome space”, with three categories, is introduced: experiences of strong trust, experiences of concern about loss of trust and experiences of broken trust. The discussion deals with the importance of the outcome space in understanding the meaning of trust in order to improve maintaining trust.