Digital content distribution systems and methods

A method for enabling a user having a first device to acquire an item, comprising:

• (a) connecting the first device to a second device, wherein the first device is a portable device;
• (b) while the portable device is connected to the second device, using the second device to submit a request to acquire the item;
• (c) after submitting the request and while the portable device is connected to the second device, receiving at the portable device an encrypted copy of the requested item and a license, and storing the encrypted copy of the requested item and the license on a first storage unit contained within or connected to the portable device, wherein the encrypted copy of the item has a header portion containing a pointer to a license server and a key-id, and the license enables a content player running on the portable device to play the encrypted item from the first storage unit;
• (d) after step (c), disconnecting the portable device from the second device;
• (e) after step (d), connecting the portable device to a third device;
• (f) after step (e), storing a copy of the encrypted item stored on the first storage unit in a content library stored in a second storage unit that is contained within or connected to the third device, wherein the second storage unit also contains a license store;
• (g) after step (f) and in response to a request to play the copy of the encrypted item stored in the second storage unit using a content player running on the third device, silently obtaining from the license server a license that enables the content player running on the third device to play the encrypted item from the second storage unit;
• and
• (h) storing the obtained license in the license store.