This chapter examines the extent to which the Internet can represent a place for negotiation, consensus building, and civic participation using Singapore’s online consultation portal and the debate over the decision to build the nation’s first casino resort as a case study. The structural design of the consultation portal and the entire content of a discussion thread with 508 posts were analyzed with a conceptual framework drawn from previous studies of democratic deliberation. Findings suggest that while the forum reflects some criteria for deliberation, the lack of transparency and government participation raises the question over the quality of the discourse and overall effectiveness of this online medium. Current challenges, recommendations, and directions for future research and development are discussed.