There has been a growing focus in UK policy discourse on pupil well being and the related concept of pupil engagement with school. This is reflected in government initiatives such as the Every Child Matters policy, which is similar to the No Child Left Behind policy in the US. This paper explores the role of individual experiences and school characteristics in determining changes in disengagement between the age of 14 and 16. We carry out the analysis by using data from two waves of the Longitudinal Survey of Young People in England and administrative datasets on schools in England. We find that little seems to affect changes in disengagement from school for the ages we are considering. However we show that being a victim of bullying and attending a school that experiences a fast improvement in its performance are clearly associated with a change in disengagement. We speculate that for the latter, the change in the school environment that accompanies improvements in performance may affect pupils enjoyment and therefore their engagement.