Tracks missing from iPod but says completely synced with Music library

Unchecked tracks are normally excluded from syncing. Have you checked for those? A smart playlist with the rules Playlist is Music and Checked is false should find any.

tt2

I was suggesting you make a smart playlist for the purpose of confirming that all tracks remain ticked.

Ctrl-clicking any ticked checkbox twice would ensure all checkboxes are ticked.

Do you have any music videos? A similar thing happens there.

tt2

You could try Edit > Preferences > Advanced > Reset warnings.

tt2

Smart playlists really aren't that difficult. You can examine the ones you have already to get an idea of how they work. I have a script call ImportDevicePlaylists that can read off the playlist from the device. You could then create a smart playlist with the rules Playlist is Music and Playlist is not <Device>\Music which should show the problem tracks.

Or it could simply be that iTunes isn't very good at counting. 😮

tt2

I just synched my iPod. I have 26,281 songs on my iTunes. Only 13,189 were synched. I had opted to synch only checked items, but only about 200 items were unchecked. A message warned me that 100 songs could not be synched because "file type unsupported"--no idea what this means, since they're mp3s I've had on my iTunes for years and have synched numerous times on my series of iPods. So that's question one. Question two is: what happened to the other 12,000-odd songs?

Sorry not to have got back sooner. I'm not sure if the 100 song count is accurate. It is a while since I saw one of those messages but I think it might mean at least 100 songs. If I recall the list it shows is limited to 100 but might not show all failures.

I cannot think of a good reason for content that previously synced to be rejected now. 😕

tt2

Yes, thank you, that's the impression I got also. I furthermore get the impression that these are actually songs that have been on my iTunes for an especially lomg time and maybe haven't been played in a while--playlists on my iPod may contain only those numbers I've played lately. Do you suppose chucking everything into a "smart" playlist might do the trick? Of course, the only way to find out is to try, isn't it? If anyone else has any ideas about this, I'd be grateful if you'd tell me.

You could try iTunes Folder Watch with its option to check for dead tracks on startup. That way you'd at least know if iTunes is properly connected to all of the content in the media folder.

You've not made use of the new iCloud Music Library feature have you? This can let you access your content from multiple computers, but files downloaded via it cannot be placed on non-iOS devices because they don't support the necessary DRM mechanisms.

tt2