A communication system 10 initialized using an iterative training portion is disclosed. The communication system 10 comprises a first transceiver 12 operable to communicate according to a digital subscriber line standard and a second transceiver 14 operable to communicate according to the digital subscriber line standard with the first transceiver 12. The first and the second transceivers 12, 14 are operable to perform an initialization 50, including a handshake portion 52, a channel analysis portion 56, and a training portion 54, the first and second transceivers 12, 14 negotiating a plurality of iterations of the training portion 54.