This paper examines the school of the future, aiming to identify and aid the implementation of the most desired version of school autonomy in Cyprus. More specifically, the study initially forecasts the areas of financial decisions that the school of the future might autonomously manage, identifies the negative effects that may appear along the way and seeks support measures that could enhance an autonomous school's efficiency and effectiveness. Moreover, after both the probable and the desired future emerge, the paper proceeds in examining the reasons causing the divergence between them, as well as ways in which the two futures may be better aligned.