At the start of preschool, four-year-old pupils differ in their development, including in their capacity to self-regulate their playing and learning. In preschool and primary school, educational processes are generally adapted to the mean age of the pupils in the class. The same may apply to pupil-monitoring systems based on information and communication technology (ICT). This norm-based factor undermines the potential of ICT to support the educational differentiation needed for pupils and increases the amount of daily work for teachers. A theoretical framework is sketched in which pedagogical-didactical, organisational and ICT guidelines enhance differentiated, self-regulated playing and learning for each pupil within preschool and primary school. To develop and check such optimal education and ICT conditions in practice, a pilot and a randomised intervention study are carried out in integrated Dutch preschools/primary schools for pupils aged 4-12. Pilot results support the use of a procedure to screen each child's characteristics at the start of preschool by parents and preschool teachers, and also the immediate relevance of criterion-based and norm-based ordering ("double diagnostics") of playing and learning materials. Intermediate results of the longitudinal intervention study empirically support the hypothesis regarding the positive effects of optimal education on the cognitive and emotional functioning of both cognitively gifted and other pupils. The discussion emphasises the need to assist schools in realising optimal education, including learners' self-regulation and adequate ICT to enhance optimal learning. Final attention is given to further development of optimal education in a European context.