iTunes on my Mac was not syncing songs nor playlists. I stumbled upon this solution. 1. Click on the small iPhone icon which is the top left hand part of the iTunes window just below the volume slider. 2. Now you should see, on the entire left side of the iTunes window, your iPhone at the top with a "Settings" (small font) list which starts with the word "Summary" 3. Make sure to click on the word "Summary" 4. To the right of this list you should see gray boxes with the following headings iPhone Backups Options 5. In the Options box, make sure to UNCHECK the "Sync only checked songs and videos" 6. Now, back to the left side menu, and click on "Music" 7. You should see another screen (to the right) with the words "Sync Music" in the tope left 8. In the box below "Sync Music" , click on either "Entire music library" or "Selected playlists, artists, albums, and genres" I chose the "Selected playlists, artists, albums, and genres" option . After doing this, I was able to successfully Sync songs and playlists. Joe