A method, system, and program for automated selection of a backup recipient and distribution of an instant messaging request to the backup recipient are provided. A communication support system detects a messaging request initiated by a requester for an intended recipient. The communication support system determines whether the intended recipient is available to respond to the messaging request from the requester. If the intended recipient is unavailable to respond to the messaging request from the requester, the communication support system searches at least one of a directory entry, a backup directory entry, and a schedule entry for the intended recipient to identify a designated backup for the messaging request. In particular, the designated backup recipient is selected from among multiple available backups where at least one characteristic of the messaging request matches at least one from among a current time period, a requester identity, and an intended subject matter specified in association with the designated backup recipient. Once the communication system selects a backup recipient, then the messaging request is distributed to the selected backup recipient, wherein the selected backup recipient is enabled then to respond to the messaging request.