Ethnographic research in innovative education settings and initiatives has shown the practical impact of modern digital life culture and conditions on both research and professional development of curriculum and teaching strategies. Following the process of digitization, themes that are high on political and institutional agenda include “IT-enhanced learning” and the necessity of synergistic organizational and pedagogical development. Ethnographic methodology enables ongoing interpretation of school development as reflected and discussed by professionals and teacher teams, thereby facilitating elucidation of changes and consequences at technical, organizational and pedagogical levels. The general question addressed can be expressed as: How can a digital platform, associated on- and/or off-line learning processes, and the context be understood, described and explored in a practical sense? Against this background, ethnographic research is challenged to go beyond the rhetoric to explore the practical implications of the digital transformation and associated discourse. The challenge has been approached in terms of practice-oriented research facing the digital culture and renewing the ethnographic approaches across the spectrum from policy- and organizational-level to practical learning-level ethnographic investigation. The challenge is also seen as embedded in research which illustrates the potentials for ethnographic multisite studies contributing to that which I express as mapping the field of practice or paradigm, and cross-case studies crossing different learning contexts. The common highlighted theme is that changes in educational systems and practices are necessitating changes in ethnographic practices.