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This paper outlines a new framework for conducting radically contextual critical digital research using a data collection system that captures screenshots of subjects’ media usage every few seconds. This affords the “radical contextualism” that approaches in cultural studies demand (Grossberg 2008), and nuanced “thick description” (Geertz 1973) to tease out the breadth of particulars defining the meaningfulness of digital media practices. It captures the order and interweaving of nearly all digitally mediated contexts, without the drawbacks of post-hoc reconstructions or ad-hoc rationalizations endemic to extant research methods. This opens up the diversity of individualized mediated contexts, and saves, in vivid detail, rapid switching across applications and contexts. After outlining the methodological strengths, it considers how this framework can both be used for digital ethnography, and to interface hyper-descriptive empirical work with contemporary digital theory (Deleuze 1992; Harcourt 2015; Cheney-Lippold 2017). Further, it aims to elucidate the ethical impacts of algorithmically curated systems on digital users, contributing to extensive growth of STS scholarship focused on this issue. It also considers the ethical bind of heavily surveillant-research to understand heavily surveillant media systems. Finally, it provides a series of vignettes describing preliminary findings and potential areas for future research.