Proactive multiple controlled-environment facility investigative data aggregation and analysis systems and methods may accept setup of alerts, each alert associated with particular data related to electronic communications, and each alert to be directed to at least one person not associated with the controlled-environment facility in which the communication originated, in which a particular resident associated with the electronic communication resides, and/or the like. Captured data related to electronic communications associated with each of a plurality of residents is received and/or retrieved and the at least one person not associated with the controlled-environment facility is alerted when the particular data related to electronic communications is received or retrieved with respect to a particular electronic communication.