A media delivery device that can automatically initiate and establish a secure wireless communication channel with an audio output device comprises a proximity module that recognizes a mutual engagement zone proximate to the media delivery device. The proximity module can detect when the audio output device is within the mutual engagement zone. Moreover, the media delivery device further comprises a communication module wherein upon the proximity module detecting the audio output device within the mutual engagement zone, the communication module automatically initiates and establishes a wireless communication channel with the audio output device. The media delivery device can then wirelessly communicate with the audio output device outside of the mutual engagement zone using the wireless communication channel.