Specific combinations of educational and ICT conditions including computer use may optimise learning processes, particularly for learners at risk. This position paper asks which curricular, instructional, and ICT characteristics can be expected to optimise learning processes and outcomes, and how to best achieve this optimization. A theoretical multilevel framework is developed to specify instructional, learning, and ICT conditions that may transform and optimise both teaching and learning. The empirical part of the paper reports on and analyses a participatory, user-oriented pilot study carried out in Dutch secondary education in the period 1999-2002. The goal was to explore how teachers can develop and practice computer-supported instructional and learning processes that are qualitatively more transparent, more flexible, and more sensitive to differences between learners, than most currently prevalent teaching practices. The pilot also resulted in a multilevel software prototype LINE which was developed to support the instructional management of learners, teachers, and school management. The outcomes of the pilot study are used to specify more transformation conditions which are required within and outside schools to optimise instruction and learning in both qualitative and quantitative ways. Finally, software functions to construct more generalised "Diagnostic, Instructional, and Management Systems" (DIMS) are modelled and discussed.