School technology integration rarely begins with school or educator choice. It is part of a wider context where external and internal factors have direct influence on the goals and tools that are adopted over time. The objective of this study is to investigate the systemic conditions that contribute or inhibit the development of different activities by teachers making use of new media. We compiled a list of well-known conditions for technology integration success and mapped these in the historical and culturally bound perspective of activity theory (cultural historical activity theory). We conducted a multiple case study analysis of four schools, public and private. The results point to unique and distinctive scenarios even when homogeneity would be expected, reinforcing the argument that material conditions do not determine pedagogical outcomes nor do they determine changes in practice. Beyond this, the study proposes a methodology that can help elicit tensions in technology integration, pointing to avenues for school development.