A messaging system, and method of operation thereof, which supports combinations of directory and mailing list addressing mechanisms. Intended message recipients are specified as declarative addresses, which may include combinations of directory and mailing list information. The messaging system includes a messaging server and an address resolution module. The messaging server receives a message from a sender system and transmits the message to the recipient system. The address resolution module, which is coupled to the messaging server, receives a declarative address associated with the message, resolves the declarative address into at least one messaging address and transmits the at least one messaging address to the messaging server. In one embodiment, a database system may be coupled to the address resolution module to allow address resolution based on information stored in a database. The address resolution module generates a database query based on the declarative address and transmits the generated query to a database system. The database system receives a database query, retrieves at least one messaging address specified by the query and transmits the retrieved at least one messaging address to the address resolution module.