The aim of this research project is to understand how parents initially feel towards sending their child to preschool, and provide possible recommendations for settings to follow to further support the parents and their child during periods of transition. A literature review was conducted exploring specific themes relating to the topic such as transition, child readiness and strategies. A sample of 6 participants, all parents of children who had started nursery were identified and email interviews were carried out. This was particularly challenging due to the low response rate. The data found from doing this was then analysed, and colour coded into recurring themes. They were then compared and contrasted to previous literature in order to validate my findings. From carrying out this research I found that the majority of parents send their child to preschool due to the pressures they experience themselves, rather than on their own child’s readiness. Another finding was that the majority of parents initially feel guilty towards sending their child to preschool as they wish to spend more time with them. Communication was also found to be a significant tool used by preschools and nurseries when supporting parents and children, especially in transitional periods. To reduce the limitations of this study in the future, the sample size would be increased. Whilst the COVID restrictions made this investigation challenging, it was still a relatively successful small-scale piece of research.