IPod error - file was not copied

When it comes to technology, if I have a piece of kit which works well and meets my needs, I am very reluctant to change it until it really, absolutely, utterly no longer works. Yes, I am a Luddite.

I am still using my old iPod Nano (ie, sixth generation iPod), which must be well over decade old, to listen to my audiobooks. I have worn out many sets of headphones, but my Nano keeps ticking on. While I do have trouble at times with syncing with iTunes, I have not yet struck a situation where I have needed to upgrade.

However, the last couple of times I have gone to delete listened to audiobooks, and to add new ones using iTunes, I got a strange message on attempting to transfer files onto my iPod from iTunes, that:

"[filename] was not copied to the iPod "[name of iPod]" because it could not be played on the iPod."

Interesting.

I deleted the books I had loaded, and reimported them to iTunes. They worked and played perfectly there. Good. Tried again. Hmm. Same message.

I went hunting for posts on this error, but the results were all pretty venerable, being between 15 and ten years old. Nothing recent (but hey, I am probably the last person on the planet using an iPod Nano). There were posts about needing to convert files again, to needing to reindex iTunes, to reimport all the files... but nothing that seemed to relate to being unable to transfer a file which had imported into iTunes perfectly, but failed to copy across to the iPod itself.

So I tried some things. I tried reconverting the mp3 audiobook files into mp3s. Reimported. Tried to copy across again. Hmm. Same message.

Then I disconnected my iPod to see if the book had turned up on the iPod in stealth mode. I found that my Audiobook player button had disappeared from the iPod. Could these problems be related? And if so, how to solve this?

I reconnected my iPod, and it showed up as normal in iTunes. I could play my audiobooks from my iPod through iTunes without difficulty. And then, when I disconnected again, my iPod audiobooks button was back on the player. And when I reconnected to iTunes, my iPod could now accept new books.

This problem must be related to deleting books from the iPod. For some reason, deleting books seems to make the iPod think that I have deleted the audiobook player app as well. Ah, well. A least I now have a work-around:

• Plug iPod in. Delete old books in iTunes
• Then play a book still on the iPod through iTunes
• Then disconnect the iPod from iTunes
• Play a book on the iPod
• Then reconnect the iPod to iTunes, and load the new books.

However, I feel I may be getting closer to having to get a new player. <sigh>

Sam