For people who know iPods and iTunes

[Tardigrade]

My Shuffle won't update any more, when I try to upload songs to it in iTunes it gives me the message The iPod cannot be updated. An unknown error occured (-50). Does anybody know what I should do to fix this problem?

[Shadow Wolf]

One of these 5 things is almost guaranteed to fix it. Behold the Five R's.

Right here.