Although an increasingly digitised society offers a variety of options, it also implies challenges, risks and dilemmas for citizens, organisations and corporations. The purpose of this article is to critically analyse digital society from the perspective of dilemmatic space. The theoretical frame offers new ways of making sense of the digital society, and may provide new perspectives on how to manoeuvre (or not) in it. By taking dilemmas as the starting point, aspects such as uncertainty, plurality, options, challenges and decision making are in focus, as are processes of power, negotiation, identity formation, positioning and manoeuvring.The theoretical framework is applied and exemplified in relation to three digitised society themes: (a) the blogosphere and social networking communities (SNC), (b) file sharing, network control and surveillance, and (c) education. These themes have been chosen in order to illustrate the different aspects of a digital society and to show how the theoretical framework operates when different aspects of these themes are placed in the foreground or background, i.e. emphasised or downplayed. This implies that the unknown and unexpected must be taken into account, and that this involves having to manoeuvre in new, changing and ever present dilemmatic spaces.