In recent decades, higher education institutions around the world have come to depend on complex digital infrastructures. In addition to registration, financial, and other operations platforms, digital classroom tools with built-in learning analytics capacities underpin many course delivery options. Taken together, these intersecting digital systems collect vast amounts of data from students, staff, and faculty. Educators’ work environments—and knowledge about their work environments—have been shifted by this rise in pervasive datafication. In this paper, we overview the ways faculty in a variety of institutional status positions and geographic locales understand this shift and make sense of the datafied infrastructures of their institutions. We present findings from a comparative case study (CCS) of university educators in six countries, examining participants’ knowledge, practices, experiences, and perspectives in relation to datafication, while tracing patterns across contexts. We draw on individual, systemic, and historical axes of comparison to demonstrate that in spite of structural barriers to educator data literacy, professionals teaching in higher education do have strong and informed ethical and pedagogical perspectives on datafication that warrant greater attention. Our study suggests a distinction between the understandings educators have of data processes, or technical specifics of datafication on campuses, and their understanding of big picture data paradigms and ethical implications. Educators were found to be far more knowledgeable and comfortable in paradigm discussions than they were in process ones, partly due to structural barriers that limit their involvement at the process level.Graphical Abstract