A computer implemented electronic out-of-office message analysis system and method are disclosed. The method includes, for each of a plurality of users, receiving a user-generated electronic out-of-office message in a natural language in which a time window of absence and at least one alternate named contact are expressed and, based on the out-of-office message, generating a structured representation of the out-of-office message which links the alternate contact to a normalized representation of the time window. The structured representation of the out-of-office message is stored in a database. From the database it can be determined whether a current user's out-of-office message conflicts with another user's out-of-office message. If a conflict is detected, the current user can be notified.