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

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.

Did the full restore, which was a lot easier than I expected. I just had to re-enter my fingerprints and credit cards.

But even after the full restore, my problem continues. Playlists that work fine on my laptop are missing from my iphone, and when I use iTunes to look at what's on my iPhone, the playlists are there and the songs are there, but the songs are greyed out and not usable.

Hmm,I know that there can sometimes be issues with playlists that have mixed content, e.g. both music and podcasts showing up for syncing or on the device. Are you using the "convert higher bitrate songs..." feature? Are you syncing over the air or with a cable? Could your computer have gone into sleep mode during the sync? I suspect something is causing the transfer to stall, and then the device is left in an inconsistent state where the menus are filled with content that isn't actually on the device.

You may find it helps to change your sync settings so that you start by syncing with a size limited smart playlist, which you then increase in size, before adding the rest of your lists once the content has been loaded up. The steps below were written with a 160Gb iPod classic in mind so you might want to start with a smaller initial size.

Break up large transfers

In iTunes select the menu item File... New Smart Playlist. Change the first drop-down box to Playlist, the next to is and the next to Music or whatever playlist holds the bulk of the content you want on your device. Tick against Limit to, type in say 10, then change the drop-down to GB, and set the last drop-down to artist. When you click OK you can enter a name for the playlist, e.g. Transfer.

Now sync this playlist to your device rather than your entire library. When the sync is complete modify the rule (File... Edit playlist) to increase the size by your chosen amount, then sync and repeat. You can experiment with different size increments, if it doesn't work just choose something a bit smaller until it works each time. Before long you should have all your music on your device. Once that's done you can move on to other media such as podcasts, videos, photos, playlists, etc.

tt2

I tried creating a playlist with one single song in it. A song that came from a CD and has never caused me any trouble. After a synch, even that one single song appeared as grey (on my computer) and was completely missing from the iphone. So that was the last straw.

Went to the Apple store and grudgingly let them do a complete factory reset of the phone. After that of course everything worked fine.

I'm surprised at how much stuff just reappears on my machine after the factory reset. I probably would have done the reset right from the start if I had known how easy it was.

But - it would be nice to know why this happened in the first place. I don't do anything weird with my itunes library, and it is not huge (about 1100 songs in all, mostly ripped from CDs). And - most important of all -- whatever it is that I'm doing I have been doing consistently for years without problems.

I'm a fellow user. I don't know why it goes wrong sometimes. I don't know why the next sync doesn't do some kind of rock solid integrity checking to make sure that every file that is supposed to be on the device is there, or the device's database is corrected so it doesn't contain entries for content that isn't there. I certainly don't know why backup then restore isn't enough on its own without having to do the slightly more complex backup, restore as new device, restore backup process. But I do know the last set of steps usually work.

tt2

On the off chance I've failed to mention it already in this thread see Backup your iTunes for Windows library with SyncToy to make sure you always have a working backup of your library.

tt2

Hi turingtest2

Is sync toy required or will iTunes backup suffice? I also have a windows app called iMazing that backs up your iPhone but it asks for my PW so I just use iTunes.

Thanks

Fredy

iTunes backs up your device's settings and data, not your media. I recommend SyncToy for backing up the iTunes library to an independent hard drive. You can manually copy using Windows Explorer, but updating a backup set by hand is tedious, and SyncToy is free. You can also use it for your other personal data, pictures, documents, etc.

tt2

Hi turingtest2

Oh Ok, I get it now, I actually already use a program called Beyond Compare and it does an outstanding job of comparing drives [or even specific folders or locations] on your system. But I use it specifically to back up my library to an 2nd external drive. and I use ITunes for the rest.

Thanks once again!

Fredy

You're welcome. 🙂

tt2

Not only did this totally work for songs not syncing to my iPhone, it also cleared the dreaded waste of space shown as 'OTHER' in the iTunes coloured bar of space on my iPhone! I got back 1.2GB!

Two enormous birds killed with the deletion of everything in the 'Purchased' folder on the root directory of my iPhone.

Amazing! Apple, please god look at this thread.

Fixed the issues I have been pulling my hair out about with iTunes lately as things wouldn't sync, the dreaded grey boxes were there with ghost files, and a ton of "Other" space filling up the drive that wasn't anywhere to be found. Thanks a ton for the fix!!! I wish Apple would fix the issue already, it's been going on for quite a while!

Jerrill, I know everyone else has already thanked you profusely for your tip of clearing the Purchases folder, but you rock. Seriously. Thing's been doing my head in for ages! Thank you!

I did find I had a couple of persistent problem albums after doing this, however these ones I was able to delete the greyed-out files in iTunes and then re-download onto the phone via wifi from the iTunes store app on the phone. I also found there were quite a few albums that, when I went into the phone, they were showing as requiring download... easy enough to do but I needed a wifi connection otherwise I'd have blown out my data usage. So it's worth just checking through your albums to make sure there aren't a heap of downloads required after you've done Jerrill's magic fix.

As an additional tip, if this has been caused by a dodgy charge socket like I suspect mine was and even decent contact cleaner doesn't seem to do the trick, a quick look on the net revealed that a wooden toothpick can be just the tool for the job - picking out a few lumps of lint that had worked their way into the socket fixed the problem.