Per Apple, the gray dot is "A bullet next to a song in your iPod shuffle playlist indicates the song is not currently on your iPod shuffle. If the song is authorized to play on your computer and is saved in a format that can be played on your iPod shuffle (such as AAC, MP3, or WAV), the song will be copied to your iPod shuffle the next time you connect it (if there is enough space on your iPod shuffle). Click here for more information."
Maybe you ripped your songs at a high bit rate and your shuffle is full?
Have you backed up your iTunes Library this week? If not, you are risking losing your music and playlists....
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