This paper presents the analysis of 292 personal stories of digital media breakdown in everyday life. The analysis identifies significant occurrences (events, incidents, processes, or issues) as identified by informants themselves; the way these occurrences are pragmatically negotiated; and the perceived outcomes in terms of cognitive, affective and behavioural effects. Against a backdrop of techno-optimism, techno-pessimism and technology as experience, the paper proposes four analytical dimensions, or tensions, common in digital media failures: the digital and the material; trust and lack of control; planned obsolescence and desirable updates; and nostalgia and reluctance to go back. While these dimensions indicate a highly ambiguous relation to digital media with the informants, the most striking observation is how the practical solution to these uncertainties is to irrevocably ‘accept and commit’ to being and becoming even more digital. That is, in the face of (a risk of) digital breakdown, individuals argue that more and upgraded digital media is always the best and undisputable response. In the light of these results, some design possibilities are suggested, including designing for nostalgia, designing for comprehensibility, and designing for failing infrastructure resilience.