Paying close attention to the intricacies of the episode below, this paper sets out to reflect in situ a shift to digitizing “lost and found” services. Foreshadowing a more extensive study on a contemporary redistribution of assistance at Deutsche Bahn, it refers to a pragmatist tradition concerned with preserving the condition of voice. Following this vein, it faces a purist critical attitude – epitomized in the practice of economics (Orléan 2014), which defends market forces (“exit”) as a way to outperform voice in any situation of decline, decay or dissatisfaction (Hirschman 1970). Anti-elitist suspicions, brought to perfection by another branch of social sciences, have become a powerful ally of this position. Rather than criticizing elitism and privilege, however, the present contribution draws on ethnographic research which displays the ambiguity of privileged users’ encounters with assis- tants. Exploring ambiguous patterns in the practice of assistance, it seeks for a politics of pity which has been largely absent from current appraisals of digital sociality.