How to fix songs still waiting in iTunes Match? I've recently refreshed my iTunes library and, as a result, decided to delete everything in iTunes Match and re-upload just to make sure it's all current and correct.  It's a large library (nearly reaching the 25,000 song limit), so the process understandably took a while and there were some duplicates to get rid of, etc.  The iTunes Match status icons helped a lot with that in terms of sorting and finding what needed to be addressed.

After a few days, however, there are still a number of songs (27 to be exact) with no discernible pattern among them which perpetually have a status icon of "Waiting" for iTunes Match.

I've tried selecting "Update iTunes Match" from the "Store" menu, closing and re-opening iTunes, even rebooting.  I can't seem to get iTunes Match to upload those 27 remaining songs.  Has anybody seen this before?  Are there other things I can try?
I would export a copy of those songs to a folder in /Users/Shared and then turn off iTunes Match. Then:


Make a new user on your Mac
Log out of your existing user
Log into this brand-new user and fire up iTunes 


It should have no music whatsoever and not be linked to your Apple ID. Now go ahead and sign into iTunes match and see what the cloud really thinks your music library looks like. Drag one and only one song from the users/shared folder into this library and leave iTunes running for a while to see what iTunes match makes of it. 

At that point you have a very isolated and potentially reproducible issue that you could reach out to Apple support in case the problem is on the server side and nothing that you were doing.