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Despite the increasing awareness of the importance of security for daily computer users, we see that many users still fail to behave securely when confronted with a security-related decision. In this paper, we introduce a new approach to security-related dialogs called Adaptive Security Dialogs (ASD). This approach is a combination of a new architecture and a new way of interacting with users to provide them with appropriate and effective security dialogs. ASD realizes this goal by matching the complexity and intrusiveness of security-related dialogs to the risk associated with the decision the user is making. This results in an architecture in which users can focus on their tasks, get (immediate) feedback on their decisions, and interact with dialogs with an appropriate complexity and appearance for the decision's associated risk. This paper makes the following three contributions. First, we introduce a general architecture for handling security-related decisions. Second, through an empirical user study using a web-based e-mail client, we show significant improvement in the care exercised by our participants without sacrificing usability. Third, we describe how the different pieces of existing research fit into the bigger picture of improving users' behavior.