Prior research suggests four privacy concern factors namely 1) collection, 2) unauthorized secondary use, 3) improper access and 4) errors in handling one’s information. This research investigates the moderating role of perceived health status on the relationship between health information privacy concern factors and one’s intentions to transact with high trust websites (offering no discount) versus low trust websites (offering high discount). We use Utility Theory to argue that privacy concern factors and perceived health status impact one’s preference of trust over discount. This is the first study, in our knowledge, to examine the impact of perceived health status in this setting. It is also an early attempt to investigate the relative role of the privacy concern factors. On theoretical side the study thus adds to the privacy-trust literature, and also contributes to the health information systems area. The study has practical implications by showing that the well known and lesser known health websites need to follow different strategies in order to win over their users’ business. Moreover, their strategy needs to be different depending upon the perceived health status of their users.