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

Jerrill's method worked for me too! I deleted the files like Jerrill said, made sure "sync music" was selected, then "selected playlists, artist,..." and the missing songs appeared on my iphone. FINALLY a solution that works!

I agree a solution that works. This was driving me nuts for the past two weeks. Thanks Jerrill!

HI I have exactly the same problem & have read this post with excitment. However I am pc-based (not mac) & need to find a program (like iFunbox) that will let me edit the purchases folder on my iPad3. Can anyone advise as I too have been unable to find an alternative solution! Considering a complete reset of iPad but a lot of work would be required presuming I could not just restore from backup as I guess it would simply restore the same problem.

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.