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

I just upgraded to iOS7 and iTunes 11.1 and now my music library on my iPhone has these weird synmbols next to certain songs, red circles with little red squares, and I'm unable to play them now. They play on my MacBook Pro but won't play on my iPhone 4. I've tried looking online but a little frustrated not knowing where to look. Googling "red circle with red square" hasn't been very helpful.


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MACBOOK PRO (RETINA, 15-INCH,EARLY 2013), OS X Mountain Lion (10.8.3), 16 GB RAM, 2.7 GHz.i7, 500 SSD, tv

Posted on Sep 18, 2013 5:49 PM

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101 replies

Nov 6, 2013 4:31 PM in response to Jerry Barrow

This from sgibbs33 worked for me. I would have spent the rest of my life trying to figure it out.


was in the same boat with 95% of my music on my iPhone showing the dreaded red square in a circle. Thanks to Jerry's post, I can see how to kick off a download playlist-by-playlist over my wi-fi. But the thought of doing that for all my playlists and for 3500 songs made me cringe big time.😠


So I kept fiddling around. I finally got my whole music library back sync'd. Here's what I *think* did it for me, but it would be good for others to try it themselves and post here if it works:

1. connect to iTunes and let it perform it's initial attempt at a resync

2. while connected to itunes, select your phone under DEVICES so that you see the 'Summary', 'Info', 'Apps', 'Music', etc. buttons at the top of the window.

3. select the 'Music' button from the top to see selections for what you want to sync. Here, I could see all the playlists that I have always had selected (prior to iOS7 upgrade). But it seemed that none of it was actually sync'd to the iPhone. So I checked one additional Genius mix to be added. Then I hit 'Sync' button at the bottom right of the window.

4. Voila! now iTunes started to successfully resync my whole music library.


My theory:

During the iOS7 upgrade of the iPhone, the upgrade process whacked the iPhone's index of music and flagged everything as being on the iCloud rather than actually in files on the phone itself. Doing *something* (anything?) to force iTunes to resync was enough for it to fix the index of music on the phone.


Interestingly, iTunes shows how much space is being used for 'Audio' on the phone. Even when the iPhone thought everything was in the iCloud, it was still using up just as much iPhone space as if the files were still downloaded.


Let me know if this works for anyone else. Good luck! 🙂

Nov 8, 2013 6:16 PM in response to Jerry Barrow

I have tried all of these suggestions and nothing works for my phone. In fact NDJerry's suggestion made it worse! It messed up even more songs than before! And the songs for me are a mix of iTunes purchases and CDs. Some very recent, some older.


I even tried deleting my whole music library from the phone, but it didn't even get rid of the songs! I can't win...they won't go away when I want them to and all won't sync when I want them to!

Nov 13, 2013 5:09 PM in response to Cleomobile

I have the same problem as everyone else, with a slight twist. WHen I try to sync, the ipad deletes all my playlists from my library. I did find how to restore the playlists, so tried again, and the ipad again deleted the playlists. I restored again, and tried to sync my phone, and it worked fine. Until oday, now 95% of the songs on my phone also have the red circle/square, and my ipad only has the songs I purchased from itunes and downloaded.


Any suggestions on how to get back the 300 plus CDs I transfered without transfering again?

Nov 14, 2013 2:01 AM in response to Jerry Barrow

Hey guys I had the exact same problem for about a month ever since I updated my phone. Finally being fed up with only being able to listen to 200/700 of my songs I decided again to try and fix it. (Mind you what I did to fix it I had tried a couple of times before but did not work for me then)


So I synced my phone and clicked into devives where there are buttons at the top which one is called music.

I then unticked everything and synched my phone.

It still did not seem to make any changes on my phone except my laptop said I lost a lot of gig.

I went back and ticked the sync all button

I then repeated those two steps another time

Something really weird happened on my phone then and it somehow started to re-download every single song which it had not done before.

It will then look like only the songs that were already working are being re-downloaded but then the ones with the red circle started coming back as well until eventually I got back my WHOLE library.


-I honestly hope it works for you guys because I know how much it *****! It may not work, as I said it did not actually work for me before until I tried a couple of weeks later. 🙂 x

Nov 23, 2013 5:20 AM in response to Jerry Barrow

The only way I can still get it to work is to check the "Convert Higher Bit Rate Songs to ###" I dont want to do that. I ripped in M4A and FLAC for a reason.



I have done everything everyone has stated. I have even deleted my libraries from itunes, deleted everything from my phone and started from scratch - rebuilding all the libraries. I started small with a couple of hundred songs, but even then only about 10 synched.



The only thing I haven't done is moved my library to a different computer - and I really dont want to do that (yet). . .not until I migrate to a new Mac.



So not happy at all. I have the 64GB phone because I rip in the non-compressed format.

Nov 28, 2013 6:31 AM in response to Jerry Barrow

Since none of these options work for me, I need to ask: What kind of file format and file size (average) are you using? I am using Apple Lossless (MP4) and the average for my music size is 35 megabytes with some of them upwards of 70 - 80MB each song.



Last week when I was in the Apple store buying a time capsule and macbook air, I asked about this. When I told them I was using files that size, they said that is probably my problem. Some devices (iPhone and iPod Nano included) can not handle files that large. Now, I have not gone back into my computer/phone to see which ones have the red circle/box and look up their file size, but until then, I have to go with what they said because nothing mentioned here works for me except for using the "Convert higher bit rate songs to xxx kbps AAC".

Dec 1, 2013 6:19 AM in response to Erik K Veland

Yes, I followed them to a "t". I even had to borrow my wife's MBA to use the PhoneView because the iExplorer on my Windows box wouldn't work.


It still did not work. Out of the 1721 songs I was trying to sync without converting them to a higher bit rate, only 586 came across.


So I decided to take your instructions one step further and totally nuke (as you put it) my iTunes (after I made copies of my libraries), I deleted everything and uninstalled iTunes. I then reset my phone back to factory settings. (Can't get more "clean slate" than that.)


After I restored my libraries from the m3u exported files, I still was only able to sync 586 songs (when not using the "convert to higher bit rate"). All of the songs sync'd fine once I checked that box.


This all leads credence to the guys at the Apple store stating that some devices can not handle the larger (very large) M4A (lossless) files.


I guess I am stuck with converting to the higher bit rate which I really didnt want to do.

Dec 1, 2013 10:57 AM in response to Jerry Barrow

i found the easiest way to fix this issue, (after an hour chatting with an itunes rep.) is to scroll down on your summary page when your iphone/ipod is connected to your computer. When you scroll you will see "Options" check the last box stating "manually manage music and videos." Then resync your phone. This fixed my problem. Hope it helps!

Dec 3, 2013 9:18 PM in response to tb212

This fixed the issue. Even though I'm still experiencing a separate issue where a few songs fail to sync "due to an unknown error".


The other method, desynching all my music and resyncing did not work for me. Like someone else mentioned previously, it actually caused more problems; more of my songs came up unplayable with the red stop button. This whole thing is very frustrating.

Dec 5, 2013 2:14 AM in response to blueblur1

Hey everyone, I have also been having this problem and have finally found a solution that is not quite what anyone else has posted yet.


I actually haven't seen the "Syncing Music to iphone" since the new ios update so im quite happy..


Here are the steps that I took to solve:


1. Turned off auto lock and password on iphone

2. After connecting iphone on the summary page the only three boxes I have checked are Automatically sync when iphone is connected, sync only checked songs and videos, manually manage music and videos

3. Now, click the On this iPhone tab. In the bottom right there are "setting" and "Autofill". Under "Settings" select replace all items when Autofilling. I also arbitrarily selected "reserve 1.12GB for disk use".

5. Then I clicked "Autofill" and selected Replace Songs.

6. Lastly I pressed "Sync" while I was still on the "On This iPhone" page.

7. I was actually about to leave the computer and then I saw something magical..."Syncing Music".....Holy Sh...!!!


Notes:On the iPhone: WiFi, Bluetooth, Cellular, personal Hotspot and VPN are all disabled. I use PC. I have about 5000 songs. I do not use Match.


Before today I was also having a disc space issue with a large block of "other". I deleted the music data from my iphone and that fixed that problem, however, the phone was still not syncing the majority (4800 of 5000) songs.


I do not pay for icloud storage


*I also do not have the "Sync Music" box checked under the Music tab, however, simply doing this did not solve the problem

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

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