Playlist on iTunes NOT syncing ALL songs to iPhone

Are you using the iPhone's Music setting screen in iTunes to manage syncing for songs? To see this screen, select iPhone in iTunes to show its settings screen in iTunes window. Along left side of screen (in the sidebar), under Settings, click Music. To the right, the iPhone's Music settings screen is shown. Is this where you select the playlists that get synced to iPhone?

Hi,

If some purchased songs are synced and some not, it could be they were bought using a different Apple ID. In iTunes, select Purchased in the sidebar and select a song. Go to File / Get info and then open the File tab. That shows who purchased the song and the Apple ID. See is there any difference between the ones that sync and those that don't, and if they correspond with the Apple ID you use to authorize the computer.

Sounds like you are setting it up correctly...

generally I purchase the songs directly thru the iTunes store app on my phone.

If you purchase (and download) them initially on the iPhone, are the songs being transferred to the Mac's iTunes library the next time you connect it, or are the same songs being downloaded to your Mac's iTunes library directly from iTunes Store (using the Automatic Download settings in iTunes preferences Store pane)?

Interesting point, but I'm not sure why that would matter (in this case), unless you sometimes have the external drive turned OFF when you use iTunes, and the missing songs happen to be on the external drive. But why would that happen; why would most song files from one album end up stored on the internal drive, and a few of its songs end up on the external drive? And if the external drive is ON, then iTunes can access its files.

On a side note, if you want to transfer all of your files to the external drive, that is certainly possible. I have it set up that way, with my iTunes folder (with the iTunes library database) staying on my internal drive, and my iTunes Media folder on an external drive. Just let iTunes move its media files. If you move the files using Finder, iTunes does not know you moved the files, so the iTunes library loses track of location for its media files.

To do this, in iTunes preferences Advanced pane, confirm the iTunes Media folder location is set to the location on external drive. Also, the TWO checkboxes for Keep iTunes Media folder organized AND Copy files to iTunes Media folder when adding to library should be checked. Then, from the menu bar, File -> Library -> Organize Library -> Consolidate files (checkbox). This command tells iTunes to copy ALL of its media files, wherever they are located, and organize them into the designated iTunes Media folder.

NOTE: iTunes makes a copy of files for the iTunes Media folder, so media files which were not already in the designated iTunes Media folder are now duplicates. After confirming iTunes is accessing its media files from the external drive's iTunes Media folder, you can delete the duplicates manually using Finder.

If it is always the same purchased songs that won't sync, you could try deleting them from iTunes and download them again. It might make the difference.

I have this same problem and the only way to resolve it is to "unsync" and re-sync all my playlists. I too would like to see a resolution to this ongoing issue.