Privacy policy statements and privacy-assurance cues are among the most important website features that online providers use to alleviate web customers’ privacy concern. This study examines the moderating role of privacy concern on how the quality of privacy policy statements and privacy assurance cues contribute to increased trust, and the subsequent decision to disclose private information online. The results of this study show distinct behavioral differences between how individuals with high versus low privacy concern form their trust to disclose private information across different contexts. The paper adds to the trust literature by highlighting the influence of the customer’s level of privacy concern (as who) and of the context (as where). The paper also adds to the Elaboration Likelihood Model Theory (ELM) by demonstrating the combined moderating roles of context and degree of involvement (privacy concern).