This article examines the recent move towards baseline assessment in early childhood education in England. From 2016, the government will introduce the use of assessment on children's entry to school (age 4-5). In this light it is significant to establish how the move towards a baseline assessment that sits within the current early years and school entry context within England. The government intend this baseline assessment to be a part of monitoring accountability and school effectiveness. Existing baseline assessment is predominantly task-oriented and adult-led and there are well-documented issues regarding the validity and reliability of this kind of data for accountability purposes. Therefore evidence building on previous assessment research will be investigated leading into a discussion on how an observation-led baseline assessment which prioritises children's well-being and characteristics of effective learning might contribute to positive early experiences of school. On this basis the article will conclude with outlining ongoing research on a piloted observation-led baseline assessment in 12 schools in South East England