After getting my iPhone 6 in early October, I was initially excited by all the cool tech in my new phone. Until I tried to sync it, that is. I eventually got so frustrated that I emailed Tim Cook for help. From that email, I wound up talking to Apple's engineers, who eventually solved my sync issues—it turns out they were related to duplicates of long-ago-purchased songs.
And for a while, things were great in iPhone 6 land. Then I ripped a few new CDs, and noticed that they didn't show up on the phone. Uh oh. Even worse, when I looked at my iPhone in iTunes, the Music section contained hundreds, if not thousands, of the dreaded gray dotted circles.
This seemingly innocent symbol means that the indicated song did not sync—the information about the song made the journey to the phone, but the song itself did not. Argh! Read on to see how I muddled through this issue, with some advice that may, or may not, help you with your own sync issues.
Read on for the gory details…except maybe for that last item, which I totally made up.