Embodiments of the present application relate generally to electrical and electronic hardware, computer software, wired and wireless network communications, wearable, hand held, and portable computing devices for facilitating communication of information. Disclosed are wireless media devices that automatically discover and automatically configure themselves to communicate with and seamlessly operate with one or more wireless devices. A backend service in communication with the media devices and/or wireless devices queries the wireless device to obtain prerequisite configuration data (P-Data) and analyzes the P-Data to generate configuration data (C-Data) that is downloaded to the media device, the wireless device, or both. The C-Data is operative to configure the media device, the wireless device, or both. The backend service may be in wireless communication with one or more of the media devices. Media devices may include a proximity detection island for detecting presence and/or proximity of wireless user devices, users, and other objects.