This paper examines how the generalization and acceleration of digital technologies in Cuba during the present century have impacted the reconfiguration of lifestyles and of the subjectivation processes of young people. It addresses the ways in which digital platforms and automation redefine job opportunities and youth working conditions;; the ways in which digital technologies have modified young people's habits regarding access to, production of, and dissemination of knowledge; and the transformations this has generated in the dynamics of domination/emancipation of subaltern identities. This research is a partial result of the project “Subjectivities in Dispute: Impacts of Digital Technologies on the Production of Subjectivities in Contemporary Cuban Society,” coordinated by the Institute of Philosophy, part of the Ministry of Science, Technology and Environment (CITMA).