This chapter investigates challenges arising from fostering new literacy with new media in an arts classroom in Singapore. The researchers designed a social networking platform and an arts authoring tool in order to foster new literacy practices via participatory culture and arts prosumption. We investigate how students spontaneously use and perceive the social networking platform and the authoring tool with a qualitative case study approach. We found that students did not approach the design as intended by the researchers – a phenomenon we identified as “misalignment between designed affordances and perceived affordances”. Students used the social networking platform as a safe Facebook while overlooking the built-in learning functions. Based on the findings, we maintain that mainstream schools may find similar issues when trying to foster new literacy with new media..