iTunes Grey Circles on Device

If your songs appear in light gray text

Your songs might appear in iTunes in light gray text for a variety of reasons. Those reasons include:

• You're not connected to iCloud Music Library. If you see a Disconnected icon in the upper-right corner of iTunes, you're not connected to iCloud Music Library. Click the icon to reconnect.
• The song isn't in Apple Music or isn't available in your current country or region. These songs also appear in gray if you search for them in Apple Music.
• Restrictions are turned on for explicit tracks. Learn more about Restrictions.
• An artist or content provider made changes or edits to an album. You might need to remove the album from your library and add it back from the Apple Music catalog.

You could try the following all-purpose steps for dealing with erratic device or sync behaviour (including the troublesome greyed out tracks and/or 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.
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, or runs iOS 11.

For added security you might also want to make an independent backup to iCloud and/or archive your current backup before you start.

FWIW I successfully used this method some time ago when Siri became unable to call contacts or play my music.

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Judging from other posts on this issue it can potentially be caused by a conflict between automatic downloads from purchase history and manual transfers, but it may also be that a sync was interrupted and the database on the device doesn't properly reflect what has transferred. My own experience last time I saw it, of switching to manual management and deleting all music visible in iTunes, wasn't successful. Some users have reported success using third party tools to dive into the device's file system and remove current media on the device then reload from iTunes, however that brings with it another set of risks, although it is potentially quicker.

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