Social media usage trends within the homeless community are not well documented. To date, few studies have examined how the poor navigate and/or build relationships in online environments, and whether these activities provide opportunities for integration into mainstream society. This study aims to fill the existing research gap by observing the usage trends of the website Homeless Nation. The objective of this study was to examine if the site aids in the development of a) digital literacy skills, b) information seeking behaviours and/or c) relationships in online communities. The data show that the site promotes relationships between the homeless community and mainstream society as well as inclusive discussions about poverty that are extrospective in nature. These findings contribute to the discussion of the digital divide, and provide insight into how social media initiatives can prevent the further solidification of social roles that segregate marginalized communities from mainstream society.