Given the variety of ways in which devices can connect to a network, and the possibility of incompatible media formats, a digital media controller implements a process through which it determines an optimal connection for playing media from a media server on a media renderer. The digital media controller attempts to connect to the media server and media renderer using the same network interface and protocol if the media server has content in formats which are supported by the media renderer. Otherwise, the digital media controller connects to the media server and the media renderer using the fastest available connections, in the event that the renderer cannot stream directly from the server, whether due to network connectivity or format incompatibility. If a direct wireless connection is available, then it is used only when the digital media controller relays and/or converts the content.