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

Scotty, iFunBox is available for Windows. I am Windows 8.1 and this worked for me.

I had this problem again even after using iFunBox and the below solution also worked.

Sign in / sign out of iTunes store on both devices got purchases that wouldn't sync to my phone to sync. I had the same dotted circles next to these songs as shown in the parent post.

This advice has turned out to be a disaster for me. While it fixed some of the greying out problems, an album I just purchased today now won't play. Sync'd backwards and forwards. Re-downloaded through Purchased in iTunes. They list in full dark text in the iTunes desktop app but they're not there on the phone. Now when I go to Purchased it displays the album with the PLAY button and when you click play the phone goes a bit mad by displaying the track but then suddenly it disappears. Totally confused iPhone now. I had rebooted the iPhone and quit and re-launched iTunes desktop app to no avail. Songs listed as present as far as my Mac is concerned but the iPhone disagrees. Argh!!!

I think the ifunhouse solution might work for me but can't figure out how to dletet files in ifunhouse. When I highlight all the files and either hit the delete key or drag them to the trash the files return. How can I permanently get rid of the files in funhouse?

I second this.  I ended up having more songs and when I clicked on one to play, it would play a totally different song (usually one 5-6 above it).  and still getting songs playing that i haven't downloaded onto my ipod.

restore here i come.

Yeah, the ifunhouse solution didn't work for me, but signing out/in on both the computer and the iphone (and then syncing) did the trick.

I tried this and it did not work. My iTunes didn't have a load of songs that I had downloaded from my phone, turns out I only had to go into the Store and click on purchases, then click on the albums for them to download.

Dude you helped me out much!!! Thanks man!!

Yes, after much head banging on this ridiculous situation, signing out/in on iPhone and in iTunes, then re-synching got things back in order.

Ron Kashden, thanks for the tip.

Apple, I'd like the hours of my life spent researching and solving this issue to be refunded to me in Apple Store credit. More importantly, FIX THIS!!

THANK YOU!!  That fixed this issue on both my iPad and iPhone!!

Yippie!

thanks!

This worked for me - many thanks.

I am having a similar problem, but it seems to be with CDs that I have imported into iTunes.  They play on my Mac book pro, but won't sync to my phone (iPhone 6) and didn't sync to my iPhone 5 either.  When I click on "on this phone" tab the songs show up as greyed out with the dotted circle.  However, there are some songs from the same album that transferred and some that didn't.  My most recent import from CD, none of the songs will sync.  When i pull them up in the library they are listed as AAC audio file.  any suggestions?

Thanks...

Jerrill - thank you thank you thank you!

I never had a problem syncing iPhone 5 before tonight's IOS 8.0.2 upgrade, which I elected to do *just prior* to syncing new mp3s.  Following the upgrade, neither my new playlist nor the files within it would sync.  Instead, I got the greyed out / dotted circle syndrome described by the original poster.

A Google search led me to your response, which led me to iFunbox.  But I thought, first, I'll take the path of least resistance, and reboot both my PC and iPhone. However, this did not fix the problem, so I held my breath, opened iFunbox, and deleted the contents from Raw File System ->Purchases.  Voila! - upon very next sync, all playlists and files showed up on my iPhone perfectly..

I don't know how you ever thought to try that particular fix, but I and the rest of your fan club are happy you did!  Thank you again for posting your workaround!

Hi All

I'm having a similar issue I think. When I tell ITunes v11.4 to copy Tracks to my iPhone5 with iOS8 from my windows 8.1 PC's iTunes Library it seems t o go well but then I notice several files never copied over.. I can wait forever and they don't seem to get there, however the track is listed with a clear dotted circle to its left. I can exit ITunes and remover and replace the iPhone and sometimes it wakes up and continues the copy but not always. I guess I need to try the file app suggested?

Any input is appreciated.

Fredy