The privacy paradox phenomenon suggests that individuals tend to make privacy decisions (i.e., disclosure of personal information) that contradict their dispositional privacy concerns. Despite the emerging research attempting to explain this phenomenon, it remains unclear why the privacy paradox exists. In order to explain why it exists and to be able to predict occurrences of privacy paradoxical decisions, this dissertation emphasizes the need to identify boundary conditions of the relationship between privacy concerns and disclosure behaviors. Across three empirical research studies varying in their contexts, this dissertation presents a total of seven boundary conditions (i.e., cognitive absorption, cognitive resource depletion, positive mood state, privacy control, convenience, empathic concern, and social nudging) that can explain why privacy concerns sometimes do not predict disclosure behaviors (i.e., the privacy paradox). The approach of identifying the boundary conditions advances privacy theories by establishing a theoretically sounder causal link between privacy concerns and disclosure behaviors while contributing to enhancing privacy policies, organizational privacy practices, and individuals’ privacy decisions.