Beginning with a reconstruction of the issues in the international debate about the ‘new’ ways of working and spatial-temporal configurations of hybrid work and organizing, this chapter traces the most recent Italian scientific discussions on this topic. As remote working practices were unusual before the pandemic, and managerial and work cultures were generally deeply anchored in traditional office work, the organizational and cultural change brought about by the flexible paradigm is particularly interesting in Italy and may lead to inequalities, contestation, and resistance. Based on some inductive traces from ongoing empirical research field on hybrid forms of flexible working and organizing in Italy, this chapter raises questions about topologies, boundaries, and mobility matters in and around organization that can help with understanding and theorizing ongoing changes of work. The insights suggest the post-pandemic need to address spatial-temporal configurations as emergent becomings through which workers make sense of organization and consider—both in theorization and organizational practice—issues of equity that can arise from hybrid forms of working and organizing.