This article shows how user-centered design can be applied to documentation and reports the results of a two-year contextual design study. The article (1) demonstrates how contextual design can be applied to information and (2) reports some of the study's results, outlining key insights gleaned about users. The study found that users vary widely in their information needs and preferences. Users employ a variety of learning strategies in learning new software and in overcoming problems encountered within applications. Documentation can better meet variances in learning styles and user preferences when tightly integrated into applications, accessible in the user's own language. Additionally, documentation is most beneficial when several assistance options exist for users to choose among, varying according to context, task, and user need. Finally, the article discusses the constraints that affect the implementation of design ideas and explores implications for practice and additional research.