compare iTunes and iPod list?

There is no iTunes utility to compare the iPod contents vs. iTunes library. If you auto-sync to a select group of playlists, you could in theory develop a smart playlist that has the opposite criteria that is used to determine which songs to sync, but that only works if you autosync to selected playlists.

If you manually manage your iPod, you cannot use iTunes to tell you the difference between the iPod and iTunes. This is a major drawback for some and I don't know why such an important tool like this was never developed. Maybe there is a 3rd party script that you could use since you use a Mac.

If not, what you might be able to do (only if you manually manage) is copy the view of your iPod's contents to a spreadsheet app, then do the same for your iTunes library, then use the spreadsheet app to tell you the difference. Not very elegant, and it will not let you load contents directly from the results (since you're viewing a comparison in a spreadsheet) but it could at least be used as a guide.

Not sure if I totally understand your problem, but a fix to what I think it is would be to create a "New Playlist Folder" via the "File" drop-down menue in iTunes itself, (named "Currently On iPod" for this example). Next, drag all the songs, and/or playlists and/or folders that you want added to your iPod into that folder. Next, make a smart playist named "Future iPod" with the rule 'Playlist is not "Currently On iPod" ' . What the "Future iPod" playlist will retrieve is everything that is not currently on your iPod. If you tick "Live updating", it will automatically refresh itself as you add more files to your "currently on iPod"folder or to your main "Music Library". This way you can automatically keep control and tabs of whats on your iPod whether you automatically or manually sync it yourself.
There are different ways to get the same effect as the one main folder example, that I could suggest, if I knew for sure that is what your original question was!

podcartuneist wrote:
Not sure if I totally understand your problem, but a fix to what I think it is would be to create a "New Playlist Folder" via the "File" drop-down menue in iTunes itself, (named "Currently On iPod" for this example). Next, drag all the songs, and/or playlists and/or folders that you want added to your iPod into that folder. Next, make a smart playist named "Future iPod" with the rule 'Playlist is not "Currently On iPod" ' . What the "Future iPod" playlist will retrieve is everything that is not currently on your iPod. If you tick "Live updating", it will automatically refresh itself as you add more files to your "currently on iPod"folder or to your main "Music Library". This way you can automatically keep control and tabs of whats on your iPod whether you automatically or manually sync it yourself.
There are different ways to get the same effect as the one main folder example, that I could suggest, if I knew for sure that is what your original question was!

P.S. The "Currently On iPod" playlist would be the one list you would manually add to your iPod or if your Pod automatically syncs, that would be the only playlist/folder that you would need to include from your iPods automatically sync list.

Ok guys, I solved this one.

1. Create a new Playlist titled 'All Music' and drag all the music from your main library into it.
2. Sync your iPod/iPhone.
3. Click the iPod/iPhone icon, Click and Highlight the Playlist: 'All Music' that was just copied over. Go to the Menu 'File->Library->Export Playlist'.
Save the File somewhere easy to access.
4. Click back to your Main Library. Delete the Playlist: 'All Music'. Go to the Menu 'File->Library->Import Playlist'. Choose the File that you just saved.

The Playlist should return but it only contains the songs that transferred over to your iPod/iPhone.
5. Create a new Smart Playlist. Set the rule to Playlist - Is Not - All Music. Click the little plus sign ➕. Set the second rule to Playlist - Is - Music.
Click the OK button. BOOM, there's all the songs that aren't copying over to your device.

Good Luck.