sync Mac book with iPod

Andrewburrell wrote:

Hi

these songs all work perfectly well on my iPhone and iPad. so clearly the iPod does not work in the same way?

The iPod does work in the same way, but if iTunes can no longer find the files for every song in your iTunes library, then when you try to synchronise a device with iTunes, it will fail. In other words, if the sequence of events was as follows, the results would be:

1. 1. Event: you have (in the past) synchronised all three devices, successfully. Result: All three play the songs without issue
   2. Event: iTunes loses track of every song in your Library. Result: iTunes can no longer play any song, but all three devices continue to play songs without issue
   3. Event: a Sync of the iPod with iTunes produces the message that you saw; i.e. some items were not copied to <x>'s iPod because they could not be found. Result: the iPod no longer has any music on it, but both the iPhone and iPad do and can continue to play the music without issue (because you have not yet tried to synchronise them with iTunes since the problem occurred)

Hence why I suggested that you check the songs in iTunes Library (before doing anything else).

It's irrelevant whether the songs work on the iPhone and iPad, check your Library to ensure that they play in iTunes.

I have to use the old way of sync files… I am wondering if the iPod is simply not compatible…

Your iPod is compatible and I don't know what you mean by "the old way of sync files". But here's a question (to ask yourself); if you "have to use the old way to sync files" (sync music to the iPod) and it works, why would you have seen the message telling you that items (songs) could not be found with the other method? Both methods would be looking for the same items.

Check the songs in your iTunes Library, do they play? Check several songs in order to discover whether it's all songs or just some of them. What do you find? Once you get to this stage, I can offer further advice, based on the answer.

The message telling you that files could not be found occurs when iTunes cannot find the file for that specific song. The message can be expanded to show a list of all the missing files, so it's possible that the reason that nothing is added to your iPod is because none of the files can be found by iTunes.

Remember, the songs are not "in iTunes". Instead, iTunes is a database that lists all the songs that you've told it about. When you added the songs, you told iTunes where the file for each song was located and iTunes uses that location every time it needs to play the song or add it to your iPod.

Start by checking whether the music plays in your iTunes Library. If a song does not play and has an exclamation mark next to the entry for it, that indicates that iTunes could not find the file. How many of your songs are affected?

When you try to play a song and it cannot be found, iTunes will ask you if you wish to locate the file. What has to be done is to locate the file and "re-attach it" to its entry in iTunes. But you need to know where that file is actually located. If it has been renamed, moved or deleted (or the path to it has been changed) that will be why the file cannot be found.

So the next question is what happened that caused the files to be lost? Did you perform any housework that involved deleting or changing those files in Windows Explorer?

Andrewburrell wrote:

my iPod is 2nd Gen - and I see that maybe there is an issue with the version OS I am using and the version of iTunes…

Let's assume (unless you tell me otherwise) that you mean a 2nd generation iPod Touch, which uses iOS (not all types of iPod do use iOS). A 2nd gen Touch can only install up to iOS 4.2.1 and that does not cause any issues with adding content to it.

One thing I failed to notice is that you're using a Macbook (I'm not a Mac user) and it's using MacOS 14.5, in which case you're not using iTunes, but instead you have Finder. Is that what you meant by the old way of synchronising with an iPod?

So you need to use Finder to add content to the iPod. Are you familiar with the process when using Finder? I believe (since I don't use it) that it's more or less the same as using iTunes, you choose what to add by setting the Sync options for each individual device within Finder.