In this chapter, the authors evaluate the use of Web 2.0 technology to engage citizens in the transportation decision making process. They evaluate the potential of Web 2.0 technology to create effective participatory environments to enable authentic participation; provide an inventory of the current tools and technologies utilized, identify barriers faced by administrators in the implementation of these tools, and summarize universal lessons for public administrators. Based on a review of 40 cases of collaborations, the authors find that Web 2.0 technology is predominantly used as a complement rather than a substitute for traditional approaches. Furthermore, the review suggests that the full potential of Web 2.0 remains untapped, and additional tools and technologies can be utilized to overcome barriers to implementation.