The disclosure describes systems and methods delivering communications based on contextual addresses. An address string containing two or more identifiers, which may not be unique identifiers, and at least one conditional operator are provided as the address for a message or communication. The system identifies contextual relationships between a plurality of entities based on prior communications between the entities over the network. Based the contextual relationships, each identifier in the address string is disambiguated to identify one of the entities as a recipient and any associated delivery conditions controlling the delivery of the communication. The communication is then delivered to the identified recipient in accordance with the delivery condition.