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Ok I learned something today. I have had this problem with the Ipod and the Zune not playing nice. Once the Zune has listened to a podcast it would delete the original file from the computers HD. Then Itunes would try and find in and then it couldn’t find it. I used Itunes to download the files. Well what happens is you get items in your playlists with a ! with a circle around it.

Well I found out how to clear them. If you try and delete them from the playlist, you can’t. If you right click the delete option is not there. Well this is what you need to do to clear these items out.

Hold down the shift key as you hit the delete key.

It is that simple. So if you search the googles and can’t find an answer this might work for your problem. I can’t tell you how glad I am to get this figured out!!!