Description: The paper is based on fieldwork in upper secondary schools exemplifying new strategies in IT-based learning and project work. The fieldwork has been carried out by means of observations, interviews and material collected in relation to three school levels: 1) The school management level 2) The colleague/teacher level 3) The teaching and learning practice level The empirical data and materials cover the school project (The Electronic School) at three levels as well as the process of teaching and learning in the IT-classes. The observations and interviews show here how i) teachers create it based strategies in the light of the professional background, ii)students in 1.g classes create strategies for IT-learning as Newcomers, where iii) learning strategies in 3.g class rather are re-created by the students as Old-timers. Methodology: The participant observation at the different school levels has involved day-to-day observation and comparative studies in different classes. This has been combined with broader field studies and discourse analysis of national policies and programmes. Thus, the empirical and analytical framework covers the spectrum from ethnography of policy to ethnography of learning. Conclusions: The paper shows how schools are facing the challenge of IT and laptops in the teaching process in order to create new routines and learning strategies - among Newcomers and Old-timers. Furthermore, the context of school and youth culture recalls the basic conflicts and dynamic contrasts of learning, such as desire/duty, playing/learning, leisure ('for leisure use')/school ('for school use'). In this light, the paper shows the empirical studies and in-depth analyses of the conflict and its practical consequences for creative teaching and learning.