Improved techniques for interaction between a host computer (e.g., personal computer) and a media player are disclosed. According to one embodiment, interaction between a host device (e.g., host computer) and a media player can be performed over a wireless channel. The interaction over the wireless channel can be used to automatically synchronize media contents stored on the media player with media contents stored on the host device. According to another embodiment, interaction between a host device and a media player, such as automatic synchronization of media contents stored on a media player with media contents stored on a host device, can be restricted. In still another embodiment, synchronization can be automatically performed when the media player is placed in a docking station that supports wireless communications.