Cable assembly including a mating connector having a plurality of communication terminals. The mating connector is configured to mate with a system connector of a communication system during a loading operation. The cable assembly includes a trailing sub-assembly having an intermediate connector and an external cable that is terminated to the intermediate connector. The cable assembly also includes a flexible cable extension having signal pathways that are terminated to and extend from the intermediate connector to the mating connector. The intermediate connector communicatively interconnects the signal pathways and the external cable. The mating connector is configured to engage a guide track when inserted into the communication system and slide along the guide track toward the system connector along a non-linear path. The flexible cable extension permits the signal pathways to bend while transferring an operative force for mating the system connector and the mating connector.