A system and method for maximizing the use of bandwidth optimization techniques in a voice-over-packet telephony system. In exemplary embodiments, the VOP system includes a plurality of telephones connected to a VOP telephony system. Upon receiving request to initiate a VOP connection, the end office switch connects to an originating softswitch for signaling functions and to an originating media gateway for transporting the media associated with the VOP connection. A connection information system accessible to the softswitch maintains connection information relating to media sessions between the originating media gateway and a plurality of candidate terminating media gateways. The connection information system may be accessed during connection initiation and advantageously used to determine whether there are nearly-simultaneously occurring and distinct media sessions having common endpoints such that bandwidth optimization techniques may be implemented.