I can't copy certain songs from my iTunes library to my iPhone despite repeated attempts

I can't copy certain songs from my iTunes library to my iPhone despite repeated attempts. These are songs I copied way back when from CDs onto my computer.  I can play them on my computer just fine in iTunes too. Status bar says "Updating files" and "Preparing to Copy" but nothing actually copies to my phone. My phone shows the songs greyed out and circles to the left of the song in the Store column and the songs never get copied onto my phone.
My guess is that there is something I am missing or something I am doing wrong.
Any advice/help is appreciated.
Thanks.
Message was edited by: dinosaur_bones_12345

screen print of issue...

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