A method and a system for contextually managing and executing a change in security behavior of a target user are provided. The system extracts multiple context attributes including activity telemetry, skill, etc., from multiple external applications. The system dynamically generates one or more security behavioral models for each user based on behavior modeling criteria. The system dynamically generates a security behavior score for each user by scoring a selection of the context attributes from their security behavioral models. The system dynamically generates targeted, contextual control elements specific to a target user identified from among the users using the security behavioral models, the security behavior score, and one or more context libraries. The system dynamically renders one or more of the targeted, contextual control elements on a user device of the target user through one or more delivery channels for executing a change in the security behavior of the target user.