This study evaluated users’ behaviors when performing inexpensive or expensive e-commerce purchases on familiar and unfamiliar Web sites. Users were more comfortable with making inexpensive than expensive purchases. They also felt more secure and that their privacy was better protected when shopping with a familiar Web site than an unfamiliar one, especially for expensive purchases. For inexpensive purchases, if the price was “right”, participants were willing to purchase the product on unfamiliar Web sites. For expensive purchases, though, the reputation of the organization hosting the Web site was the most important factor. In both cases, privacy was a minor determinant for deciding whether to make a purchase from a Web site. Only 20% of the users regularly accessed the sites’ privacy policies during their interactions with the sites. Moreover, less than half of the participants even looked at privacy-policy links during their interactions with the Web sites.