Improved techniques for interaction between a host device (e.g., host computer) and a portable media device (e.g., media player) are disclosed. According to one embodiment, interaction between the host device and the portable media device can be performed over a network. The network can include wired and/or wireless components. The network can also be local, regional or global in geographic coverage. The interaction over the network can be initiated by the portable media device, manually or automatically, so as to request a content update from the host device. In response to the requested content update, updated content is received at the portable media device from the host device, provided a network connection between the portable media device and the host device is available through the network.