Q: What are these red circle symbols that suddenly appear in my iTunes library on my iPhone?

Well, if this isn't the solution for you, maybe someone else's is. I had tried unchecking Sync all songs and then rechecking it. They were still on there after both operations, including the songs with the red circles/squares. But when I opened my Music icon, and opened the list that appears on the bottom of the screen on the far right (icons for Radio, Playlists, Artists, Songs and then three dots in a row) a list of items appeared:  Albums, Audiobooks, Genres, Compilations, Composers AND Shared (interesting since husband's iPhone doesn't have that tab). I opened Shared where it listed the name of my iPhone and the name of my iTunes Music. I was sharing only with my iPhone. Now I am sharing again with my iTunes and all songs are appearing. YAY!

Exactly. That's what people don't understand. Some of us want this music on there, not just to hide it because the symbols are irritating. That's not fixing the problem.

I'd like to try all of these options but all of a sudden I have playlists disappearing from iTunes on my computer and random songs being removed from other playlists, also on my computer.  Before I try and get my iPhone to sync, I need help figuring out whythis is also happening.

Thanks very much for posting. This fixed the problem YAY!!!! I had to un sync twice before it would remove the songs from my phone but it worked the second time. This problem seemed to occur after upgrading to itunes version 11.1.4.62 thanks again :-)

This issue has been driving me insane. I bought a refurbed 5th Gen 32GB touch, and originally set it up using my backed-up version of my older iPod. Got the dreaded red circles and gray-ed out songs.

So I did a factory wipe twice, and set it up as a new iPod, twice. Same problem. Also tried many of the solutions in this thread.

So my boyfriend did a DFU back-up/recovery mode and we set it up again, a third time. Same problem.

Each time I tried to sync my music (approximately 3,500 songs), it would start to sync and then randomly stop. After tinkering around, we finally got it to "work" by just syncing a few songs at a time. As in, one or two artists per sync. This seems to have fixed the issue for now, but it is going to be a really long and tedious process to get my full library back on to my new iPod...

So what fixed my red circle, red square issue is:

Connected my phone to iTunes

Clicked: File --> Devices--> Transfer purchases from iPhone.

I don't know what else this did but what I do know is that all the songs that had the red circle, red square are present and able to be played.

Thanks NDJerry, this fixed my issue!

This worked for me. alisjo865.

Except for one song. I have that song 'unchecked' on my iTunes list anyway, but wonder 'what on earth?'

Thanks for posting this!!!1

Im having the same issue now, never had it until the recent iphone and itunes updates.  I have tried switching to manually managing music, clicking on the "download all" button in itunes on the iphone, nothing seems to get the songs to sync on to the phone!  I brought my phone in to a genius bar and their answer was "we can't tell you what the problem is unless we have the PC here too" then they wiped my phone and re-installed the software, sent me home but now even more songs arent copying over.  FIX YOUR SYNC ISSUES APPLE!  This is so annoying, I didnt buy a large memory iphone just to not be able to play music offline.  That was the freaking point of buying a larger memory device.  Ill try transferring purchases from the devices view in itunes next but way to make your users irritated apple!

Tried a number of the other fixes but yours worked.  Simply take all the music off the iphone, put it all back on again and voila!  The iphone equivalent of fixing your old TV by turning it off then turning it back on again

I just wanted to post that this method WORKED. I had this problem for months and nothing did work. Finally, I found this thread and I'm ecstatic to find that this worked. If this was reddit I'd give you gold.