Q: Dotted circles next to songs, won't sync, red circle with square?

I had this problem (dotted circle, songs greyed out and wouldn't play in iTunes after I had bought them on my iPhone and tried to sync to my PC).  I solved the problem by going into the iTunes Store and clicking on Account.  After signing in, I clicked on Purchase History and found my recent purchases ( 4 songs) were marked as HIDDEN (***??).  I was able to click on "UNHIDE" and then went back into my library and the songs were there-  no more dotted circle!

Now my question is, WHY would Apple "Hide" my purchases from ME??

That's not working for me

No idea if this will help, but I fixed my dotted circle problems by messing with the "autofill" sync settings when my iPhone was plugged in and it resolved the issue. 

I had the same problem and I solved my problem with deleting the recent songs I added to my iTunes one at a time.  I had my iPhone plugged in to my Mac while I was doing it and I was keep deleting song after song to see which one caused the problem. I figured out that I deleted the right song because my iTunes suddenly synced all of my songs to my iPhone out of nowhere! So I suggest :

Plug in your iPhone to your Computer

Delete every single song you added recently one after another to find the one that caused the problem (I would also delete it from your computer)

Your iTunes should start sync your songs automatically once the "damaged" song is deleted!

I then put all the other songs that I already deleted back to my iTunes library and voilá no problems it synced them with no problems. I hope that helps! Cheers.

OK, I was so frustrated with this issue, when I resolved it, I felt that it was my duty as a human being to share with my fellow man. So, you need to connect you iphone to itunes, via chord. Then you open you itunes library. Select whatever songs/playlists that you want on your iphone (I just selected my entire library because I had alot of storage and didn't want to mess with finding each and every song that was having problems). So, select the songs, and drag them over to your iphone icon in your itunes.

Once you do this, you have to sync you phone again (via chord). For some reason I had to do it 3 times because I got a couple of errors and it didn't work on all the songs the first  couple of times. Anyway, it worked after 3 tries and all 1741 of my songs play on my iphone now. Good luck.

I had the same issue, before this happened my iPod was hooked up to my brother's computer. Since he went off to college-took the computer-had to hook up with a different computer. After that the red circle issues started. The second time this happened was a few hours ago, but I found out how to fix it. Plug the iPod into the computer, turn WiFi on, and open iTunes. Go to the iPod click on music go to the playlist uncheck it then click the box to check it then hit sync.I had my iPod opened to the playlist and after it synced I scrolled through my list and there was no more evil red circles. Hopefully, this will work on yours. I asked my sister if she had this problem with hers, because she has the same iPod and she told me, "No." I think the cause of the problem is what year the iPod was bought. I got mine the year it came out (2012). My sister got her's at the end of 2014.

I tested one of the songs on my iPod that had the evil red circle and my iPod shuffled several songs until it found one that I can listen to. Does your iPod do that?

I found the elegant solution to this.  Download iFunbox.  Go to the "Raw File System".  Go to the Purchases folder.  Delete whatever is in there.  Everything syncs up properly and the nasty grey dotted circles go away.  There is either a corrupted file there or there is some type of copy write control that has gone haywire.

Works perfectly.

dj

FIXED MY SYNC PROBLEM:

Finally found out why all of my music wasn’t syncing….. After the short sync time, a box would come up stating that there were “errors” when syncing. They were 14 tracks that had been deleted, but were still somewhere in a playlist.

If your getting a sync error message, and there was a problem with some tracks.

• Take a screen shot of the “error” list.
• Go to your Library, click on Music, then Playlists.
• Search for and delete each individual track name from the "error" list.
• Click on iPod and “Sync” again.

Pretty silly that it wouldn't just skip those tracks and sync the rest. Hope this helps.

I have found another solution to this, or at least the possible cause of the problem. For me when i took the phone off of "sync music by wifi", everything immediately started syncing. Nothing else worked for me.

Rename the song's album in your Music library (ie. "Album Name CIRCLES") and sync your iphone/ipod. Once your iphone/ipod has synced rename the songs back to what they should be in your Music library. Sync your iphone/ipod again to solve this issue.

I ran into the same issue of having sync problems between iTunes and iPhone rendering the red square and red circles next to 90% of my songs.

I'm using a MacBookPro running El Capitan, 10.11.2, with iTunes 12.3.2.35 and an iPhone with iOS 7.1.2

As my trouble started after adding 3 CD's to my iTunes Library and adding those albums to my iPhone Playlist I started to work from there. What solved the issue for me was that I added manually a large artwork to an album (5 Mb). After removing the artwork, resizing it (in my case to 500 Kb), adding the artwork again. This solved the issue for me.

None of the above worked for me, unless deleting and adding files to library and syncing is included.