iTunes store importing music to iphone, exclamation mark problem

You've posted in iTunes for Mac, but your product line says Windows. Which is it?

You should add all of your media to your iTunes library, back that up, and then sync selected content to your device. Dragging directly to the device from Finder or Explorer may or may have worked with various builds, but it isn't the intended method, and might be one of the reasons you've been able to create duplicates.

Here is a way to locate the tracks with exclamation marks and eliminate them.

Lost & Found Playlists

Create a playlist called Found, select everything in the Songs view in Music and drag it into the Found playlist. Create a smart playlist called Lost matching All the rules Playlist is Music and Playlist is not Found. Your lost tracks will be in this playlist. Select all with Ctrl+A then use Shift+Delete to remove.

Or use iTunes Folder Watch and enable its option to check for dead tracks on startup.

If you want to fix them instead, assuming that is possible, see Re: iTunes can’t locate my music files.

See also this post on Re: Deleting duplicate tracks which covers various pit falls that you can run into deleting tracks manually and includes a Windows script for an automated approach.

tt2