It is an object of the present invention to send information accurately to a target person having a plurality of e-mail addresses or contact points. A delivery server 10 is provided for sending an e-mail selectively to a target person having a plurality of e-mail addresses. The delivery server 10 predicts a target person's condition when sending the e-mail, orders the plurality of e-mail addresses in descending order of likelihood that the target person will receive the e-mail, and sends the e-mail according to the ordering. Furthermore, it is configured so that the next ordering reflects the e-mail address where the target person has received the message as a result of sending the e-mail.