Since iTunes version 7, many iPod Shuffle 1G owners have been facing synchronization issues making the smallest iPod simply not usable anymore.
As mentioned by Denis and others, flashing green or orange lights, as well as a typical "Error 1418" message were the main symptoms of this problem. Several users have launched dedicated topics on Apple forums and even some websites, such
1418hell.com, were created simply to make this problem publicly known and acknowledged by Apple.
Some Cupertino engineers (especially
RoyB) have decided to analyze this problem; and thanks to logs provided by many Shuffle owners they were able to release an updated Shuffle firmware that should fix the issue.
Direct link:
iPod shuffle Reset Utility 1.0 for Mac