As today, it is more and more the digital that groups and amasses us, this paper turns to Sigmund Freud's Mass Psychology and the Analysis of the ‘I’ to address a range of questions: what is the social (the group); what is its relation to the herd (or the mass); what is an individual; what is the latter's relation to the social and/or to the mass; and what, if anything, changes on all these levels in digital times? To answer these questions, the following claims are made: psychoanalysis is not an individual psychology, psychoanalysis is not a social psychology—psychoanalysis is a mass psychology. The paper first scrutinises how Freud's subversion of the traditional question ‘how does a mass become a group?’ eventually positions the figure of the Leader at the junction of subjectivity and intersubjectivity. From here we move to Jacques Lacan and two of his early writings in which he tries to conceive of leaderless groups and of subjectivation beyond the reference of the Father (‘Logical Time and the Assertion of Anticipated Certainty: A New Sophism’ and ‘British Psychiatry and the War’). On the one hand, this allows to assess the current digital massification processes. On the other hand, the fact that we conclude that psychoanalysis itself cannot offer an algorithmisable model of the becoming on (inter)subjectivity, should be our prompt to take a political stance.