This chapter aims to provide an overview on the relationship between overtourism and technology, shedding light on the perverse effects of technology when addressing overtourism. An exploratory study was adopted because one should move away from the formal testing of hypotheses and attempt to analyse the key issues around the core concepts we are concerned with, i.e., the dark side of technology when addressing overtourism and its links to theory. The aim of this chapter is, therefore, to take a broader look at this thematic, and thus broaden the discussion around this topic. Results point out the fact that, although technology can be used to better manage overtourism, it is also linked to fashion trends, and several tourism destinations find themselves promptly overbooked in result. The originality of this chapter lies in the fact that unlike other studies, this research focuses on uncovering the dark side of technology, which has generally been promoted as the ideal tool to mitigate the impacts of overtourism. This critical overview might help both scholars and practitioners to reflect on and/or rethink how technology is really helping the destinations to overcome the challenges that come with overtourism.