This article reflects theoretically on the conditions of possibility for critical work to be conducted in the context of the digital humanities and aims to provide a broad conceptual vocabulary suitable for supporting and expanding this rapidly changing subdiscipline. It does so by elaborating on the framework of critical technical practice (ctp) first proposed by Philip Agre, suggesting how this notion might be connected productively with philosophical lineages of antipositivist epistemology, but as such traditions are reimagined and retooled for today’s informational contexts. Here, ctp is considered through the work of sociotechnical problematization, especially by the various techniques that differentiate existing infrastructural solutions on the basis of the purported material problems and difficulties they claim to address. The origin of Agre’s notion of ctp is linked back to its inspiration in the specific methodologies and concepts in the work of Michel Foucault. It is also suggested that other important connections to the thought of Henri Bergson, Gaston Bachelard, Georges Canguilhem, and Gilles Deleuze can be made. While presenting a rich set of resources for the consideration of sociotechnical problems, the argument is made that these resources might be productively placed in dialogue with existing digital methods and techniques through a reflection on media aesthetics. The article concludes by illustrating the relevance of this general framework with reference to a number of projects by media practitioners relevant to digital humanities, including the work of Rosa Menkman, YoHa, Julian Oliver, Dmytri Kleiner, and Esther Polak.