Grounded in uncertainty reduction theory, the present study analyzes the content of 50 privacy policies from well-known commercial Web sites with a view to identifying starting points for improving the quality of online privacy policies. Drawing on traditional content analysis and computer-assisted textual analysis, the study shows that privacy policies often omit essential information and fail to communicate data handling practices in a transparent manner. To reduce Internet users’ uncertainty about data handling practices and to help companies build stable relationships with users, privacy policies need to explain not only the data collection and sharing practices a company engages in but also those practices in which companies do not engage. Further, more exact lexical choice in privacy policies would increase the transparency of data handling practices and, therefore, user trust in World Wide Web (WWW) interactions. The results also call for less verbose texts and alternatives to the current narrative presentation format.