iPod How can I delete "orphaned" files from iPod Nano that don't appear in iTunes?

[magentawave]

- iPod Nano (Latest generation)
- iTunes 12.0.1 (Latest version)
- OSX 10.9.5

I'm having issues with my latest generation iPod Nano and iTunes that I don't think were there before I updated iTunes to 12.0.1...

1) When my iPod Nano is connected to my computer and opened in iTunes most of the iPods playlists are empty or almost empty. Yet, when I disconnect the Nano from my computer/iTunes, I can see all the files that should be there. Does anyone know why this is happening?

2) I have 14 "orphaned" podcast files that appear in my iPod Nano Podcasts list when the Nano is NOT connected to my computer/iTunes that do not appear when the Nano is connected to my computer/iTunes. Can someone tell me how I can delete those files?

3) Is this something that can be fixed if I update my Macbook Pro to Yosemite?

Thanks

 

[magentawave]

Anyone?

 

[Jessica Lares]

Have you tried pressing the sync button when it's connected?

 

[magentawave]

Yes and those files that don't appear in the Podcasts when I connect the Nano to iTunes are still visible in my Nano's Podcasts when I disconnect from iTunes. Do you think I will need to do a factory reset on the Nano?

Have you tried pressing the sync button when it's connected?

 

[Jessica Lares]

That might be the best choice yeah. Have you always been ejecting it properly when hooking it up? iPods have always had issues like these.

 

[magentawave]

This iPod is only a couple months old and I'm pretty sure I have ejected it properly every time.

 

[magentawave]

I have an update. The problem I was having was that I couldn't delete podcasts from my latest gen iPod Nano because when I connect my ipod to my computer there are no podcasts there to delete...even though there are clearly podcasts in the iPod when its not connected.

The update is that I hit the "Restore iPod" button and reloaded everything but I'm having the same problem as before.

QUESTION:

Is there anything else I can do to remove the podcasts or is this proof that my iPod is defective and that I should return it?

Thanks

 

[jruschme]

I'm thinking this is an iTunes library problem, not an iPod one. Is it possible that the podcasts in question are appearing in the regular library as regular "songs"?

Have you, by any chance, moved your library recently?

 

[PinkyMacGodess]

I'm thinking this is an iTunes library problem, not an iPod one. Is it possible that the podcasts in question are appearing in the regular library as regular "songs"?

Have you, by any chance, moved your library recently?

That's what happened to mine.

 

[magentawave]

Thanks for replying.

No I don't recall moving my iTunes library. I'm not sure these are relevant to my original issue but I have a couple questions please.

1) When I open iTunes on my Mac and go to iTunes > Preferences > Advanced: You will see in the image below that the box is checked for Copy files to iTunes Media folder when adding to library. Should that box be checked? Does checking that box mean that I am unnecessarily filling up my hard drive? What would happen if I unchecked that box?

2) On my Macs hard drive, when I go to Music > iTunes > Previous iTunes Libraries: You will see in the other image below 6 itl files in the "Previous iTunes Libraries" folder. You can also see the big red arrow pointing to what I assume is the most current iTunes library. I'm thinking that when I update iTunes that it creates a new itl file and puts the older one in the Previous iTunes Library folder. Is there any reason I shouldn't delete the 6 itl files in the Previous iTunes Library folder?

3) I use a program called YoutubeToMP3 that downloads stuff from Youtube and automatically converts those files to mp3's and then it drops those mp3's into my iTunes Music folder and go to a playlist named "=YT Audio" and then I put them on my iPod. These are interviews, etc. that I listen to one time and then delete. The problem is that deleting them from the "=YT Audio" playlist doesn't delete them from the iTunes Music folder which results in filling up my hard drive with tons of junk I don't want. The only way I know to delete them now is to go into my iTunes Music library and do a search and then delete them one at a time. Thats a hassle. Question: Is there anyway I can designate that when I delete a file from the "=YT Audio" playlist ONLY that it automatically deletes the files from my iTunes Music folder / hard drive?

Thanks again.

I'm thinking this is an iTunes library problem, not an iPod one. Is it possible that the podcasts in question are appearing in the regular library as regular "songs"?

Have you, by any chance, moved your library recently?