Disclosed are embodiments of a system and method for automating the exchange of information between the multiple personal computerized devices of an entity so as to provide context for communications, such as incoming and/or outgoing telephone calls, with other entities. The system and method associate one entity with multiple devices. Communications over a device (e.g., one of the various types of telephones) are tracked. Then, for a given communication, an identifier (e.g., a caller ID from an incoming telephone call) is communicated to at least one other device. The other device performs a local and/or internet search for information associated with that particular identifier. The retrieved information is then displayed so as to provide the entity with essentially instantaneous context for the given communication. The system can be implemented using client-server network technology or, alternatively, using point-to-point communication technology.