Music on my iPhone has a perforated circle around it and will not play

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.

tt2

If the ‘perforated circle’ looks anything like this (I interpret it as a circled exclamation mark)

then that would be a sign that the source file is not on a mounted local disk, so that the reference in the playlist points to nothing.

A “Song Info” (Right-click/Control-click in iTunes on the Mac) would invoke a dialog box to locate the file. Choosing ‘No’ would bring up the Song Info of the unattached song anyway without the link. The File tab will show the last known location of that file, among other details.

I have seen this occasionally on my iPhone/iPad while viewing their contents through iTunes (I presume that's what you're showing above). I'm not sure of the cause of this, but I've narrowed it down to a few possible causes:

1. iTunes purchases made directly from the device. When I've done this, sometimes the purchase seems to be left orphaned as a grayed-out item when viewing my device's contents through iTunes.
2. As above, sometimes I'll change the tag information (in my library) from what the original purchase had when I bought it from iTunes. This sometimes creates an orphaned version of the original purchase on my device, I suppose because it thinks it is no longer on my device because the tag is different (but this is not always the pattern).

In either case, what has helped is to use 3rd party software to delete a hidden "purchased" folder within the iOS device. I'm not at my Mac right now and don't recall the name of the program, but it is a popular one and I chose it because of a specific thread in these forums where a well-respected member of the Community (Chris CA) used it for the same reason and solved this problem for him too. I'll see if I can find more info and report back.

You woukd start by selecting the icon for the device where it appears to the right of the media selection drop down tool. This then gives access to the Summary tab mentioned, where there are controls for managing the types of backup and restore that are performed.

tt2

Select the device with this icon first:

Then you should be able to find this list:

tt2

This thread suggests that it means that your device doesn’t have enough free storage space to complete that sync, and the marked songs were excluded from the copy procedure.

Unfortunately, it is not listed at iTunes for Mac: Symbols used in iTunes. I have send feedback, so hopefully the list will get updated.

Thanks, it was iExplorer.

Here is the thread that led me to the solution in my case:

Re: iPhone songs with dotted circle and greyed out info

iFunBox is one that is both free and cross platform. Decline any free offers that come along with the install.

tt2