Embodiments of the invention are directed to a system, method, or computer program product for cross-channel electronic communication security. In this regard, the invention provides dynamic construction and targeting of adaptive simulated malicious electronic communications for unsecure communication identification by a user. The invention configures adaptive simulated malicious electronic communications for interacting with users via user interfaces of the multiple electronic communication media and user devices. Another aspect of the invention is directed to configuring, dynamically and in real time, a simulated malicious electronic communication for one electronic communication medium, based on and in response to, user actions on another simulated malicious electronic communication on another electronic communication medium. Another aspect of the invention is directed to escalating, in real-time, a level of authentication required for the user to execute the user activity based on user actions performed on the simulated malicious electronic communications.