A method, system, and program for automated distribution of an instant messaging request for an unavailable intended recipient to a backup recipient are provided. A chat support system detects a particular messaging request from a requester for initiating a communication with an intended recipient who is unavailable to respond to the messaging request and, in response, the chat support system selects a backup recipient designated to receive the particular messaging request. The chat support system then directs the opening of a communication channel for a messaging session between the requester and the backup recipient. Then, the chat support system detects a message log of at least one message entry for the messaging session between the requester and the backup recipient. The chat support system then updates the intended recipient with the message log, such that even though the intended recipient is unavailable to respond to the messaging request, the intended recipient is enabled to monitor the resulting messaging session between the requester and the backup recipient.