Research into sustainable assessment highlights that students must not only learn to evaluate their final products and performances but also the processes of learning they engage in while producing these final outputs. However, what is missing in this research is a focus on practices – the specific activities that are undertaken in completing tasks – and on how these are adapted to different, increasingly technologically-mediated environments. The capacity to improvise, to work around or subvert formal or expected procedures, and effectively adjust working practices, is critical for learning to operate across different situations, with different combinations of people, technologies and systems. Drawing on examples from sociomaterial research in educational and clinical environments, we argue that developing evaluative judgement of working practices will help students to overcome some of the challenges of moving between university and professional settings. To this end, we propose a reconfiguration of assessment to encourage visibility, creativity and dialogue around the idiosyncratic activities that students engage in while learning.