Community civic engagement is a new and emerging trend in urban cities driven by the mission of developing responsible citizenship. The recognition of civic potential in every citizen goes a long way in creating sustainable societies. Technology is playing a vital role in helping this mission and over the last couple of years, there have been a plethora of social media avenues to report civic issues. Sites like Twitter, Facebook, and other online portals help citizens to report issues and register complaints. These complaints are analyzed by the public services to help understand and in-turn address these issues. However, once the complaint is registered, often no formal or informal feedback is given back from these sites to the citizens. This de-motivates citizens and may deter them from registering further complaints. In addition, these sites offer no holistic information about a neighborhood to the citizens. It is useful for people to know whether there are similar complaints posted by other people in the same area, the profile of all complaints and a know-how of how and when these complaints will be addressed. In this paper, we create a conversation-based platform CitiCafe for enhancing citizen engagement front-ended by a virtual agent with a Twitter interface. This platform back-end stores and processes information pertaining to civic complaints in a city. A Twitter based conversation service allows citizens to have a direct correspondence with CitiCafe via “tweets” and direct messages. The platform also helps citizens to (a) report problems and (b) gather information related to civic issues in different neighborhoods. This can also help, in the long run, to develop civic conversations among citizens and also between citizens and public services.