Digital technologies are likely to be appropriated by the homeless just as they are by other segments of society. However, these appropriations will reflect the particularities of their circumstances. What are these appropriations? Are they beneficial or effective? Can Skype, as a case in point, assuage the social disconnection that must be, for many, the experience of being homeless? This paper analyses some evidence about these questions and, in particular, the ways communications media are selected, oriented to and accounted for by the homeless young. Using data from a small corpus of interviews, it examines the specific ways in which choice of communication (face-to-face, social media, or video, etc.), are described by these individuals as elected for tactical and strategic reasons having to do with managing their family relations. These relations are massively important both in terms of how communications media are deployed, and in terms of being one of the sources of the homeless state the young find themselves in. The paper examines some of the methodical ways these issues are articulated and the type of ‘causal facticity’ thereby constituted in interview talk. The paper also remarks on the paradoxical problem that technologies like Skype provide: at once allowing people in the general to communicate but in ways that the homeless young want to resist in the particular. The consequences of this for the shaping of communications technology in the future are remarked upon.