In this chapter, we carry out a critical review of the various historical analyses of the impact of technological interventions in education. The purpose is to analytically explore and learn from some of the methodological limitations and strengths of the approaches adopted to measure and capture the impact of educational technology. This retrospective examination is then used to explicate methodological design principles that can increase the use and value of research evidence regarding the impact of educational technology. Capturing and understanding the impact of digital technologies in and on learning is inherently problematic. It is exacerbated by the continually developing nature of digital technologies and their formal and informal boundary crossing. We posit methodological design principles that are sympathetic to the fact that evidence of the pedagogical application of digital technologies is both borne out of, and brought to bear in, complex and dynamic contexts that are mediated by, and impact upon, the various ways in which technologies are appropriated for educational purpose. The chapter concludes with a call for methodological perspectives that are not confined by paradigm, but are able to bridge and integrate research paradigms in order to respond to the complex sociocultural ecologies within which digital technologies are implicated.