If you have a first gen iPod Shuffle and have been hit by the bug that prevents playback of music downloaded from ITMS, Apple has posted a fix
which you can install to address the issue. The flaw, which reared its head a while ago, could cause songs either to skip or be completely unplayable. The “iPod Shuffle Reset Utility 1.0.1” can be now be downloaded
at your leisure. This update applies only to the first generation of iPod Shuffle, and not newer models.