Cannot transfer music folder to Itunes Library

You need to copy all of the files that are in the F00-Fnn folders into your computer, unhide them, the move them into the Automatically Add to iTunes folder in your media folder (normally Music > iTunes > iTunes Media > Automatically Add to iTunes).

tt2

You put files that you want to add into:

../iTunes/iTunes Media/Automatically Add to iTunes

iTunes will either add them to the library and move them to somewhere like:

../iTunes/iTunes Media/Music/<Album Artist>/<Album>/## <Name>.<Ext>

Or they get moved to

../iTunes/iTunes Media/Automatically Add to iTunes/Not Added/<Date & Time>/<Whatever they were originally called>

tt2

See Recover media from an iPod - Apple Community. Specifically you need to unhide the hidden items recovered from the device before you can add them to an iTunes library. Generally adding them to the Automatically Add to iTunes folder will then work to absorb them into the library and arrange the files according to their metadata.

tt2

Copy the suspect items into the Automatically Add to iTunes folder inside the iTunes Media folder. They will either be added to the library or moved into a Not Added folder. Assuming they are not added you will know for sure that iTunes is rejecting them, even if you don't know why.

tt2

I posted this already. Recover media from an iPod - Apple Community. My personal experience has been that iTunes ignores the files in hidden folders, although that could potentially differ between Mac and Windows. Despite what that article says I would copy the files to your computer and unhide them rather than attempting to get iTunes to import them directly from the device.

As for extracting playlists from the device that normally requires third party software. I've written a script for Windows but I don't think there is a parallel for Mac. You can see what is on offer at Doug's AppleScripts iTunes.

tt2

See Import media from a computer to iTunes on Mac - Apple Support.

tt2

Here is a screenshot of the folders on my iPod classic. Anything that is greyed out is hidden. Once you have copied all of the F## folders to your computer they need to be unhidden before iTunes will be able to import them and their contents.

tt2

Apple support aren't geared up for giving advice on media recovery from their devices. Me I'd just copy the F## folders from the device, unhide them, and import that media to the library. Note if you're getting that 1,477 count when you try to drag the whole device folder to iTunes then you'll likely be counting non-media files as well as what is in the device's music folder. That is the only one that counts. Everything else is going to be support files on the device.

tt2

If they are already on your computer but seem to be ignored when you try to add them to iTunes try Repair security permissions for iTunes for Mac - Apple Community.

tt2

iTunes supports the transfer of purchased content from the device to the library, but not other content you might have ripped from CD or obtained from elsewhere. The method I give of extracting the contents of the F## folders should include all items that are on the device. That assumes they remain present in the file system and haven't been erased by other actions that have been taken.

tt2

Personally I would always to use the free Finder based method. I've personally rescued data for several friends and colleagues over the years, and others here have used my user tip to recover their data. Try SynciOS if it is supposedly free and see how you get on. I seem to recall another user posting about success with it recently.

tt2

The Not Added folder is only used for content placed into the Automatically Add to iTunes folder. If you add content in any other way iTunes will simply ignore anything it doesn't like.

tt2