The pressure towards digital education is felt everywhere including in places with extreme digital divides. Resource-constrained educational environments are particularly threatened by datification manifest in the dominant business models of surveillance capitalism as there is less room in such contexts to refuse the 'free' offerings from big tech companies; it is these very contexts which are most vulnerable. Yet educators within such environments are not mere pawns of circumstance. While the realities of their structural constraints may be invisible or obfuscated, educators are driven by their own 'concerns', which in this case pertain to the needs of diverse students in very challenging circumstances as well as to their personal aversion to being monitored. This paper reports on findings from focus groups in a mixture of institutionsin South African education. Archer's theoretical framework provides a lens to show how, despite very little choice, educators critically reflect on their circumstances expressing discomfort and unease.