Songs are greyed out with a dotted circle next to them and won't sync

Try the following all-purpose steps for dealing with erratic device or sync behaviour (including the troublesome grey dotted circles of stalled transfers). They assume that all of the content you want on the device is in your library ready for restoring. If it isn't see Recover your iTunes library from your iPod or iOS device first. I would also recommend you copy everything out of the camera roll if you haven't already.

1. Backup device to iTunes.
2. Restore as a new device.
3. Restore the backup you made earlier.

Use an encrypted backup (*) if you want to preserve passwords, Wi-Fi settings, web history and health data where appropriate. I also suggest syncing with a selection of playlists (unless you're using iCloud Music Library) rather than manually adding content as, if nothing else, the process above is easier to do if you ever have to go through it again.

(*) The downside with backup encryption is that if you forget the password when you need it again, which could be years later, you may need to invoke a workaround to turn off encryption as shown in Re: disable encrypted backups, which can only help if your device is in a state that can backup to iCloud.

tt2

I tried downloading iFunbox but it wouldn't install because Norton blocked it. Said it had a virus. I tried downloading three other versions of it, and none of them would open. SO, I used AnyTrans, which is a great software btw, to delete the files in the "Purchases" folder, and went back to iTunes...but my files that are grey STILL will not sync. I am so frustrated. Why do some sync and some don't?! Is it the ipod cord? Very, very frustrating.

The process is usually very effective. Restoring and reloading is a standard troubleshooting approach with Apple devices. What anti-virus software do you have, if any? These can sometimes adversely affect communications between iTunes and the device. Are there any error messages when you try to reload the content? Are you trying to sync it over Wi-Fi rather than USB?

tt2

I noticed w mine I had switched to "manually manage music and videos" to handle an issue I was having transferring files. When I disabled that so it switched back to using iTunes, everything synced up the way it was supposed to.

I downloaded one of the file explorer programs (iFunbox in my case) for my PC and deleted everything out of the "Purchases" folder on the phone's "Raw File System". After a couple of syncs with iTunes everything was back to normal. It appears that something was screwed up on the iPhone side that iTunes couldn't sort out. I don't think anything could sync from iTunes to the phone, not just the greyed out items.

This is why resetting and restoring the iPhone also works for a lot of people. It's overkill though, deletes your app data, and just wastes your time setting everything back up after the restore. Better to use the surgical approach of a file system explorer program on your PC to fix what appears to be a mundane data corruption issue.

Jerrill, you are my HERO!!! I have been trying to figure out how to get those blasted grayed-out circle songs off of the "On This iPhone" tab on iTunes, and NONE of the advice given in the other threads has worked. So I downloaded iFunbox and piddled around and finally found where they were in the Raw File System and followed your instructions. They're gone!!! And I even synced again a few more times to make sure they didn't pop back up! I screamed WOOOHOOOO and woke up my husband who came running in the room terrified that something horiffic had happened to me. You made my day! Thank you!

Thanks Jerrill, this worked for me after I tried everythign else except restore. I think there are a few issues with how the itunes DB works- needs fixing APPLE!

Yup totally worked for me.. Apple itunes engineers should look at this post...

This worked for me as well. Thanks for taking the time to share. I love the internet!

This has also solved a syncing issue for me where playlists were not working correctly. For some reason it screwed up the album artwork on podcasts but unsubscribing and resubscribing did the trick. Apple should really sort out some sort of database error tool.

Thank you, Jerrill. After hours and hours looking for a solution, your method actually did the trick.

I downloaded this program but how do I get to file section you are talking about?

I downloaded ifunbox. What are the steps to get rid of the greyed songs? I can't seem to get rid of them.

Thank you Jerrill, worked perfectly!!!

connect the device and delete everything out of the "Purchases" folder on the phone's "Raw File System" folder.