The objective is to examine parent’s expectations and concerns about upcoming transitions, as well as how parents describe their children in transition. Research has shown that the time before and after school start can be seen as an important period of life. Transitions can also pose a particular strain. Although children often are well prepared, they can “get lost in transition” when exit and entry processes in different school forms are floating into each other. Therefore, support from parents and teachers could be considered as crucial. The analysis is built on theories of transition and socio-cultural perspectives where surroundings, relationships, critical events and contexts become important. The data consists of 173 questionnaires answered by parents to children who are about to make the transition to school. The questionnaires were answered a few months prior to the actual transition, when the head masters invited the parents to visit school and to get informed about the preschool class. The parents could choose whether they wanted to participate in the study or not. The results show that even though the parents seem excited about their children’s next step on the educational ladder they also describe certain concerns. The most reoccurring theme in the narratives is the descriptions of the big and competent preschool child who becomes a small school child in need of care after the transition to preschool class.  Hearing parent’s concerns and understandings about their children in transition informs us how we can prepare both children and parents for transitions.