Things That Suck
Initial posting: 2019-09-08
For more than five years, this has plagued all iTunes users for syncing music from the iTunes library on a desktop computer to iPod, iPhone, and iPad. Here are just a few posts from frustrated users regarding this.
Dec 5, 2012: https://discussions.apple.com/thread/4573038
Jan 5, 2013: https://discussions.apple.com/thread/4676111
Apr 15, 2017: https://discussions.apple.com/thread/7925928
Mar 26, 2018: https://discussions.apple.com/thread/8333944
I also have been running into this problem frequently because I have an MP3 music library on my desktop computer that I synchronize to my iPhone through a series of smart playlists in iTunes for Windows.
Here's what I find a little strange. iTunes obviously knows about those songs with dotted circles. Otherwise, they wouldn't be displayed. So why isn't there some code in the synchronization process that can handle these cases rather than simply showing a dotted circle? Sometimes, subsequent manual synchronizations resolves these, but not always.
These are the two ways I found to get these back onto my iPhone.
1. Delete the original song from iTunes music library, resync the music to the iPhone, then add back in the song, then resync again. Doing this removes the song from any manually-created playlists that it was added to, so it's necessary to take the extra step to add the song back to playlists. Of course, this requires yet another manual sync to the iPhone.
2. From a suggestion from discussion thread 7925928, locate the song on the iPhone associated with the gray circle in iTunes. Click it to play it. The song will be grayed out on the iPhone playlist. Then resync in iTunes. Again, this is a painstakingly long process, especially since you need to do a lot of searching in iTunes to locate the dotted circles, since there is no way to sort the dotted circle column to group them all together, and then on the iPhone for the song and then play it to make it turn gray.