Match process stalling out at end

That’s about the point, where I am. Except, I have yet to talk to a senior AppleCare advisor, as the last two times they were supposed to call me, the call was hung up on their end, without anyone calling back.

I had also been told to turn iTunes Match everywhere, where it gets accessed. I did, but I am not sure, that it did any good.

I just got off the phone with AppleCare. It was my nth call on the issue, but only my 2nd with a senior AppleCare advisor. The previous advisor had recommended

1. quiting iTunes,

2. moving the iTunes Media folder outside of ~/Music/iTunes, and

3. trashing all iTunes preference files in ~/Library/Preferences/ . I was then supposed to

4. re-launch iTunes, so that new files would get generated in both of those locations,

5. quit iTunes again, and

6. put the iTunes Media folder I had put aside back in its proper location.

When I launched iTunes again, the matching process started and all the previously stalled files uploaded to iCloud properly and were able to be downloaded on all other devices that were logged into my iTunes Match account.

What did not work, however, was the automatic matching process that starts, when a new file is added to iTunes manually. This process stalls somewhere in the "Delivering iTunes Match results” step.

During my second conversation with a senior AppleCare advisor we documented this, and the case has now been escalated to “Engineering.” At the beginning of this call the advisor admitted that I was likely dealing with an issue that Engineering was already aware of and was working to fix.

In the meantime, selecting “Update iTunes Match” from the iTunes “Store” menu does work for me. Since I don’t add new files to my iTunes library too often, it’s not too big of a hassle.

At last, iTunes 12 has been the fix I've been hoping for - so far at least! Right click > Add to iCloud finally works again, and very fast 😀

Go to songs, and uncheck all the boxes with issues. This solved my problem.