A server-based system enables exchange of medical messages between users, monitors for a probability of communications breakdown likely to result in medical error, and instigates corrective actions to prevent communications breakdown from occurring. Monitoring may include whether a user has read or acted upon a message received within a specified timeframe and whether a user has specified routing preferences for delivering a message to a user better suited to read or act on the message. Corrective actions include the determination of and routing of messages to an optimal recipient and the generation of alerts to subsequent users where a message has not been read or acted upon within a specified timeframe.