This paper investigates the factors that affect users’ communication satisfaction within a virtual community, in particular, an online chat room. A research model consisting of 3 aspects—psychological, technological and environmental—is developed to examine effects of anonymity, media richness and activeness of chat room on social presence, privacy concern, and further communication satisfaction. We leverage on well established theories such as self awareness, SIDE model, social presence, and the institutional theory theories to make our arguments. Results from a survey conducted to test our model suggests that higher self anonymity decreases privacy concern, while higher others anonymity increase in privacy concern. We also confirm that richer media leads to an increase in social presence, which, in turn, influences privacy concern negatively. Lastly, results support that privacy concern and social presence are determinants of communication satisfaction in online chatting.