A complex view of the socioeconomic digital divide in urban schools requires us to address not only the gaps in access to technology, but also inequities in access to human support, digital content, and "effective pedagogical" approaches to technology integration. This study explored the use of social networking site (SNS) as a platform to provide a supportive human and social infrastructure in an urban educational context. The use of SNS was compared with the mainstream course management system (CMS) by urban teachers in terms of the "education", "esthetic", "escapist", and "entertainment" aspects of their learning experience. The study results suggested a high degree of learner engagement in all four aspects of participants' use of SNS, whereas the esthetic and entertainment realms of experience were found to be the weakest components of the mainstream CMS. These findings contribute to current understanding of repurposing popular open source technologies for teaching and learning in socioeconomically disadvantaged urban schools. (Contains 2 tables and 3 figures.)