Prior research has explored homelessness and barriers to accessing digital technology. Our study will build on this evidence base by moving beyond a discussion of what technology is used, to better understand how these technologies are used, and the content and nature of communicative practices within homeless communities. This will be done by drawing together two important streams of homelessness research. The first stream focuses on the importance of connectedness for homeless persons. The second stream concentrates on the importance of identity for homeless persons, recognizing the negative impact of homelessness on an individual's self-concept. Through the lens of boundary objects theory, technology-mediated social interaction will be viewed as providing a safe environment where homeless persons and service providers can develop mutual respect. The insights gathered will inform future interventions that aim to facilitate better social interaction among homeless persons, non-homeless persons, and the formal institutions supporting the homeless.