A method includes: applying an unsent electronic message to an electronic screening tool programmed to identify content that is potentially not authorized by a business or potentially harmful to the business; generating, based on an application of the unsent electronic message to the electronic screening tool, a risk assessment score for the unsent electronic message; determining that a value of the risk assessment score exceeds a threshold value; and following a determination that the value of the risk assessment score exceeds the threshold value: generating an electronic alert message for a sender that indicates that the unsent electronic message comprises content that may be objectionable.