Songs Don't Get Added Correctly To My Nano From My iTunes Playlists.

Some of the songs from my iTunes playlist don't get imported onto my Nano for some reason. I tried over and over--first deleting the playlist, then adding the playlist again to my Nano, but the same songs still don't get added correctly. They show up on the Nano's playlist, but when I try to play the song, it skips them!

The gray dot means the songs didn't get synced...
What's the provenance of the songs?
What's the format/encoding/bitrate?
If you can’t load a song or other item onto iPod shuffle
The song might have been encoded in a format that iPod shuffle doesn’t support. The following audio file formats are supported by iPod shuffle. These include formats for audiobooks and podcasts:
AAC (M4A, M4B, M4P) (up to 320 kbps)
MP3 (up to 320 kbps)
MP3 Variable Bit Rate (VBR)
WAV
AA (audible.com spoken word, formats 2, 3, and 4)
AIFF

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