Music files don't copy from iTunes to iPhone, appear grey with a dotted circle

When I drag music files from iTunes (desktop) onto a connected iPhone, many times the files just don't copy to the iPhone - the tracks appear in the list on iPhone, albeit grey and the most-left column is a dotted circle with a to me unknown meaning (it might be a progress bar really...).

iTunes 12.0.1.26 (OS X Yosemite)

You can see some of the files copied, while others did not, in the screenshot:

enter image description here

The dotted circles are in the left-most column.

I'll list some things to rule out:

  • Not using iTunes Match.
  • I do have enough space on the iPhone. It's a new iPhone 6 Plus 128 GB, with about 60 GB free space.
  • I do have "Manually manage music and videos" selected.
  • I can copy some files, some files just won't copy. Even in the same drag manoeuvre, some files would copy and some will not.

Ignore all the rest of this crap, all I did was change the name of one of the songs that wasn't syncing. After I did that I hit sync and they all started syncing. Hope this works for whoever reads.


I've observed this issue with several iPod Touch devices (one V1, one V4). It only started for me when I moved my music files from my main PC HDD to a Wi-Fi connected NAS.

My workarounds are as follows:

  1. I don't copy more than one album at a time (manually manage music).
  2. I wait for the previous copy to finish before starting a new one.

When I do get items with the grey circle, I sync the device. At the end of the sync process, iTunes will start copying the missing items to the iDevice. It may take several syncs to clear up the issue, but it should eventually get your items over.


You guys. I solved this. I don't know if this is the right or only way to fix this problem but it worked for me. It took forever, but it worked.

Delete all of the songs of your iPod/iPhone that have the little circle.

Drag them back onto your device, one by one.

It's the only way it worked for me! If I tried to drag a bunch of them it never worked.

I hope this helps someone!