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

THAAAAANK YOOOOOU!!!

Absolute hero! Jerrill deserves a medal for this!

Just be aware that FAKE ifunbox sites exist. I fell for one and ended up with a bunch of Malware on my MBP. Had to do a system restore. : (

Almost perfect!!!

Many thanks for the help. Nontheless I still got a few songs (less than before) marked with dotted circle.

Have repeated the deletion of Purchased content more than 3 times and no change.

While adding new list will increase the number.  Went all over again and again, the number is reduced, but still there are songs under that characteristic.

Hope Apple will solve one day. Hope to be alive by then

OK, I got i Funbox, but when I cannot seem to delete the purchases. They appear to still be there even after I select all of them and delete.

How do I get rid of these files?

mczink

Ditto, that for Jerrill! It was driving me nuts. Deleted everything in purchases using iFunBox and all is well. Thanks so much. iTunes is still a nightmare.

You're a hero, Jerrill! That drove me nuts trying to fix it. Now I see nothing but the music I recently synced. No more "ghosts." Thanks and Happy New Year!

Just wanted to give a shout out to Jerrill. Many thanks. Your recommendation worked.

iFunBox worked brilliantly for me on my iMac (running Yosemite). Everything with a grey circle now syncs perfectly and I was FINALLY able to get some music over to my phone.

However - for any of you Mac users out there beware that iFunbox will ruin Safari, and prevent it from functioning outside of safe mode. MAKE SURE YOU HAVE GOOGLE CHROME OR ANOTHER BROWSER INSTALLED BEFORE YOU USE IFUNBOX!

After you use iFunbox to fix the syncing issue, you can delete the program and it's components, then finish cleaning/restoring function of safari by using a simple Adwaremedic to get the rest of the junk it leaves behind, as noted in another discussion here: safari continues to quit unexpectedly after downloading ifunbox

This is an amazing solution! My phone was showing all my songs just fine, but some songs were grayed on in iTunes on playlists. I downloaded ifunbox, followed your steps and wiped out over 700 purchases, restarted iTunes and re-synced....all was perfect in less than 5 minutes total!!

Thanks Jerrill!!!

Apple, take note of this solution and just fix it in your next release....you cannot call something "genius" in iTunes when the elementary functionality is lacking....

Used ifunbox to delete files from the Purchase folder, but the problem did not go away.

I never purchase anything, so I don't think the problem started with Purchases.  Is there another folder I should delete instead?

Generally if syncing doesn't work as expected take the following steps:

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

This assumes all content on the device is in your library. If that isn't the case see Recover your iTunes library from your iPod or iOS device.

tt2

Step3 says  "restore the backup made earlier"

How much earlier?  Do I have to find a backup that was made before I noticed this problem?  It's been over a week since I noticed the problem -- will my cloud backups go back that far?

Step 1 says "Backup device". This is the backup that you are going to restore. You've just made sure it is up-to-date by following step 1 before you get to step 3.

It is worth noting that until the moment you restore a device what you actually have is one rolling backup set. It gets updated with changes each time you ask iTunes to backup, or during the first sync on any given calendar day. Mac users have the ability to clone existing backups, but on a PC the only way is to run a backup-restore cycle, after which the restored backup set is archived and a new rolling backup is created for that device. Doing so say once a month is probably good practice. That way if you don't discover that you've deleted something important until after the device has backed up then there is at least a chance that you could restore an older backup, export the lost information, and then restore the "current" backup.

tt2

Another thanks for this information.  It look me a little while to be able to delete the files simply because this iMac keyboard has no delete key (fn+shift+backspace I found out).  I took a deep breath, deleted everything from the Purchases folder, connected my iphone and did a synch.  Just as you said, all the greyed out files have gone.