We investigate the complexity of mutual interaction between learner, teachers and educational software developing new approaches for educational content adaptation, personalising the support and educational services to teachers and learners. Our aim is to create new opportunities for knowledge communication and learning meeting unique and specific needs, characteristics and preferences of individuals, groups and communities . We employ state-of-the-art technologies, such as ontologies,† artificial and nature-inspired intelligence paradigms, user modelling, and data mining, aiming to strike a balance between technologies, learners/teachers and their environments, between adaptation and accommodation.