Systems, methods, and articles of manufacture embodied as computer program products for facilitating the avoiding of sending a message to an unintended recipient. In some embodiments of the invention, in an instant messaging (IM) environment, the relatedness of a first entry in a first IM session to previous entries in the first IM session is determined. In response to the entry not meeting a first pre-determined relatedness threshold, an alert is issued. In one embodiment, the relatedness of the first entry to previous entries in a second IM session is determined, in response to the entry meeting a second pre-determined relatedness threshold, an alert is issued. In one implementation, relatedness is determined based on a matching of keywords between the first entry and the previous entries. In another implementation, relatedness is determined based on a matching of topics associated with one or more IM sessions, which topics can be associated with keywords.