Many of my song in my playlist have a red square in a circle

after syncing my iphone, many of the songs in my playlist have a red circle with a red square in the middle

Hello now80,
Thanks for using Apple Support Communities.
For more information, take a look at:
iTunes: Troubleshooting issues with third-party iTunes plug-ins
http://support.apple.com/kb/TS3430
iTunes won't open or quits unexpectedly
You see this alert while syncing: "... cannot be synced. A duplicate file name was specified."
If you see the above symptoms or other unusual behavior, you can disable any third-party plug-ins by opening iTunes in Safe Mode:
OS X: Hold down Option-Command.
iTunes: How to re-create your iTunes library and playlists
http://support.apple.com/kb/ht1451
Note: After re-creating your library, any devices that you sync with iTunes (Apple TV, iPod, iPhone, iPad) will see your iTunes library as a new library and will completely resync.
Have a nice day,
Mario

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