This publication presents abstracts and abstractions developed through a workshop held at University of Cambridge, and organized in collaboration between transmediale festival, Aarhus University, and Cambridge Digital Humanities Learning Programme. It presents a critical inquiry into new technologies of feeling, recognizing that digital culture has become instrumental for capturing and managing what Raymond Williams’ would once have called “structures of feeling”—referring to lived experiences and cultural expressions, distinct from supposedly fixed social products and institutions. It focuses specifically on the domain of machine learning and on the ability of technologies to capture and structure feelings and experiences that are active, in flux, and in the present.