Error message while copying from iTunes to iPod

My daughter's iPod shuffle (1st gen) was not charging so I updated it to the lastest software (1.1.5). While doing so, iTunes required an upgrade as well (7.5). Both are updated. But it is still not charging. That's my first problem.
I decided to see if it was a problem with my computer. So I tried using my other daughter's iPod. It was charging and playing music. While I was at it, she wanted to add new songs. For some reason I had difficulties so I updated her iPod software to 1.1.5 as well.
When I went to put songs on it from iTunes, I get an error message "<song name> was not copied to the iPod "<ipod name>" because it cannot be played on this iPod.
I now have an iPod that has no music on it. (Plus a second iPod that's not charging.) Both iPods are about 15 months old. They are shuffles (1st gen) and we have XP on our computer.
Can anyone help.

Some formats that play in iTunes are not compatible with the 1st generation iPod shuffle, Aiff and Apple Lossless for instance. Apple Lossless is not supported on the 2nd generation shuffle: iPod shuffle: Compatible audio formats
I don't use a shuffle but it has a function that other iPods don't have, on-the-fly conversion, the option to "Convert higher bit rate songs to 128 kbps AAC". You should check this out, this should save you converting your lossless files in iTunes. You can find details on pages 12 and 13 of the manual: iPod shuffle User Guide
Quote: "If this option is selected, songs encoded in AIFF or Apple Lossless format are
converted to 128 kbps when transferred to iPod shuffle (the song files in iTunes aren’t
affected). Otherwise, iPod shuffle doesn’t play songs encoded in those formats"

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