iPod Classic has error (-42408)

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I have an iMac OS X version 10.6.8 and I lost 90% of my songs in iTunes and last time I synched my ipod classic, the songs were wiped there as well.

So...I use the time machine and eventually got all the songs back, now trying to transfer (synch) my ipod but I get a message "Error iTunes (-42408).

What does this mean and how do I fix it.

Many thanks in advance for your help.
 
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Mac Mini i5 (2014 High Sierra), iPhone X, Apple Watch, iPad Pro 12.9, AppleTV (4)
Is your version of iTunes up to date? If not, that's the first step.
 
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Yes I just recently updated iTunes...10 I think it was.

But when I connect my ipod, it no longer opens in iTunes, which means I cannot edit any of the stuff I have on it.

Note: I am still getting this error message when I open iTunes (-42408).

Cheers.
 
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Thanks chas_m I have already been to that link and many others, still no joy.

Still haven't been able to find my specific error number.

Cheers.
 
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Many thanks louishen, I successfully downloaded from the link you provided (took 3 hours...slow connection) but unfortunately when I restarted my computer and opened iTunes, I got the same error message and it still will not recognise my ipod.

The iTunes version now is 10.6.3

Any other ideas would be most appreciative.

Cheers.
 

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