If you see an error indicating your songs may not be licensed for transfer:

This might be an issue with Yahoo! Music Unlimited subscription music if you are trying to transfer subscription music. Your subscription music licenses are renewed automatically, but in some cases, you may need to manually renew them. This might occur if you have not logged on for several weeks. If you have an up-to-date subscription to Yahoo! Music Unlimited and you see an error message when trying to transfer subscription music to a device, or your songs on the device will not play, try the following:

1. Sign in to Yahoo! Music Unlimited. Be sure you're online.
2. Download a Yahoo! Music Unlimited subscription song, or play a previously downloaded subscription song from My Music while online.
3. Reconnect your portable device. When the name shows up in the left pane, your device should now be updated.