Abstract: A computer system enables a business to support the automation of out-of-office (OOO) messaging when a recipient of e-mail is unavailable. An out-of-office message configurator operates in co-operation with the e-mail application for out-of-service messaging so that configuration information is automatically requested to specify the content of an OOO message before a first person logs off the computer system. The configured OOO message may then be analyzed to verify that the message complies with a set of rules such as an e-mail policy in a business environment. Consequently, when an e-mail message is received from a second person and the first person is unavailable, an OOO message may be returned to the second person. Different variations of an OOO message may also be selected based on the specifics of the second person.