In an approach to detecting the transmission of messages, analyzing said messages, calculating a message risk score and transmitting a warning notification, one or more computer processors detect transmission of a message from a user to a selected recipient. The one or more computer processors extract message information from the detected message. The one or more computer processors retrieve one or more historical conversations between the user and the selected recipient of the detected message. The one or more computer processors determine a risk score corresponding to sending the detected message to the selected recipient based on applying the extracted message information and the retrieved historical conversations to a cognitive model.