iPod iPod only partially loading audiobooks

[rskoefod]

My iPod Classic has always successfully loaded the 40-odd audiobooks that I have purchased in my iTunes. But I recently synced it, and now it is only putting about 10 of the audiobooks on the iPod and leaving all the others off. There is plenty of room available on the iPod drive, I have the option to sync ALL audio books selected, and there is no problem syncing any of the other music files/songs in my iTunes library. I have not changed any settings as far as I know. Any thoughts/suggestions? Thanks!

 

[Grumpus]

What OS are you using? Are you syncing with iTunes, or with Finder? If iTunes, what version? Which iPod Classic do you have? Is it possible that the missing audiobooks have ended up as music (possibly under 'unknown album')? Have you tried putting the iPod into diagnostic mode and checking the SMART status to see if the disk is still feeling well?

 

[rskoefod]

I am using iTunes (version 12.13.3.2) on a Windows 10 (version 22H2,OS build 19045.4894) pc. iPod Clasic is 7th Gen with 160 GB drive. I don't see any books in unknown albums. Disc appears to be well (also, there is no problem syncing files other than the audiobooks). Also, I have 2 iPod Classics that are doing exactly the same thing - so it seems like it is somehow related to the iTunes software or settings or something rather than the iPods themselves?

 

[Grumpus]

Also, I have 2 iPod Classics that are doing exactly the same thing - so it seems like it is somehow related to the iTunes software or settings or something rather than the iPods themselves?

That sounds reasonable.

I've seen reports of audiobooks which didn't originate from the iTunes store failing to sync, but you said yours came from the store.

I don't have any great ideas, but here are a few things to check:

With one of the audiobooks that fails to sync, if you right click it in iTunes and select Get Info, does everything look ok? Is the media kind "audiobook?"

In iTunes on macOS, you can right-click a song or podcast (and I assume audiobook) and select Show in Finder to see the actual media file on disk. For you it may say Show in Windows Explorer, or words to that effect. If you do that for an audiobook that failed to sync, is it found? Do the permissions look ok for the file?

With an iPod connected, can you drag and drop one of the audiobooks that failed to sync to the iPod? Does it sync ok in that case?

With an iPod connected, look in the Summary section, where you can change various Options (like Enable disk use). Is there an option that says Sync only checked songs and videos? If so, and it's checked, try un-checking it.

I have no audiobooks, but maybe this weekend I can scare one or two up to see if I can think of anything else.

 

[rskoefod]

Thanks so much for your help. I have discovered the issue. For some reason the files for most of the books I purchased from iTunes are no longer in my iTunes library. Have no idea why they have disappeared.