As one of the scales which assess the end-user’s security behavior, the security behavior stage model (SeBeST) [1] is a practical approach to characterize similar groups of users (precontemplation, contemplation, preparation, action and maintenance stages) and provide customized remedies to improve their security behavior. For example, in OS update message customization, a group that does not update OS continuously may require a message indicating the ease of OS update; on the other hand, updating users need a message indicating the importance of OS update. In this paper, we propose a personalized OS update message interface based on SeBeST. We conduct two online surveys to evaluate effective appearance and message as the personalized user interface (UI). First, we assess the interface’s appearance individually for the three behavior stages (preparation, action, and maintenance) and then combine the customized messages and the selected impressions for these stages. We confirmed that appropriate appearances are different for each stage. For example, a highlighted red button is efficient for users in the preparation stage. On the other hand, the red background is suitable for users of the action and maintenance stages. We discovered that the combination of the message indicating the disadvantage of the OS update and the UI which is the highlighted red button is suitable for the preparation and action stages. In addition, we confirmed the best combination for users of the maintenance stage is a message indicating the ease of OS update and the UI which is mouse over pop-up representation. Therefore, it is necessary for each user to show the appropriate message and UI.