A method for enabling access to digital rights managed (DRM) content from a server to a portable playback device using a device that functions as a proxy for enabling communication between the server and the portable playback device. The method provides for establishing a connection with a device capable of operating as a gateway device for passing data between the portable playback device and the server, requesting that the device establish a connection with the server and operate as a proxy for enabling data exchange between the portable playback device and the server, sending to the server, upon establishing the connection with the server via the device operating as a proxy, data indicating DRM solutions supported by the portable playback device, and a list comprising requested DRM content to be downloaded to the portable playback device, and receiving from the server, via the device operating as a proxy, the requested DRM content and DRM rules associated with the received content.