© Springer Nature Switzerland AG 2019. There is a growing acceptance of the association between obsessive, compulsive and excessive usage of digital media, e.g., games and social networks, and users’ wellbeing, whether personal, economic or social. While specific causal relations between such Digital Addiction (DA) and the negative life experience can be debated, we argue in this paper that, nevertheless, technology can play a role in preventing or raising awareness of its pathological or problematic usage styles, e.g. through monitoring usage and enabling interactive awareness messages. We perform a literature review, with the primary aim of gathering the range negative life experiences associated with DA. We then conduct two focus groups to help gather users’ perception of the key findings from the literature. Finally, we perform a qualitative analysis of experts and practitioners’ interviews and comments from a user survey on DA warning labels. As a result, we develop eight families of the negative life experiences associated with DA, examine the role of software in facilitating the reduction of such negative experiences, and consider the challenges that may be encountered in the process.