This article tells the story of “LinkVan,” a project that explores approaches to participatory technology design to forge more equitable digital and social relations in the Downtown Eastside (DTES) community of Vancouver, British Columbia. LinkVan began as a project to create a literacy-friendly online service directory for low-income and homeless citizens. We trace the experiences and patterns of digital inequality that led to the formation of the project and describe the evolving approach to technology design oriented to “the direct involvement of people in the co-design of the technologies they use” (Simonsen & Robertson, 2013 p. 2). We consider insights from 58 user experience interviews that suggest the precariousness of access, the centrality of digital literacy education in participatory technology design, and the potential of side-by-side ‘conversations at the interface’ (Attar, 2005; Barbatsis, Comacho, & Jackson, 2004) to imagine new digital landscapes and new social relations.