Techniques for supporting USB and video communication over an extension medium are provided. In some embodiments, an upstream facing port device (UFP device) is coupled to legacy connectors of a host device, and a downstream facing port device (DFP device) is coupled to a USB Type-C receptacle of the sink device that may provide both USB and DisplayPort information. The UFP device and DFP device communicate to properly configure the USB Type-C connection for use in the extension environment. In some embodiments, a source device is coupled to the UFP device via a USB Type-C connection, and legacy video and USB devices are coupled to the DFP device. The UFP device and DFP device again communicate to cause the source device to properly configure the USB Type-C connection for use in the extension environment.