So Many iTunes Match Issues—Part 1

iTunes Match freezes at “Sending information to Apple” stage

This would be fine, except that attempting to change metadata of certain songs throws up the “iTunes Match has not yet blah blah blah this file yadda yadda yadda” message.

I tried following g8tecrasher’s tip at to get past this first-stage error and, miraculously, it worked.



The way Match handles ‘duplicates’ is a whole bunch of crazy. It is not OK for iTunes to throw up its hands and protest that The Thrill is Gone from Completely Well is the same as The Thrill is Gone on a different album unless iTunes is also going to symbolically link the original version of The Thrill is Gone to Completely Well. Otherwise, the following clearly unacceptable behaviours can occur:

1. I have random 4* songs in a playlist. If the duplicate version of The Thrill is Gone finds itself in that playlist, the whole playlist becomes inaccessible from matched devices.

2. If I delete the “duplicate” version of The Thrill is Gone and then play the album Completely Well, guess what song doesn’t play? Now my Completely Well is, well, incomplete.

Presumably, the problem that Apple is (hamfistedly) attempting to fix is that I might fill up my 5 GB allowance of iCloud storage with a thousand files of the same song from different albums. Assuming that this is really a problem that is crying out for a solution, and given that iTunes already has done the work to link these two files together (in order to determine that one is a duplicate of the other) why not keep one physical copy of the file and as many symbolic links to the same file as the user wants. This avoids unnecessary storage consumption while not creating the horrendous user experience problems of Apple’s current ‘solution’. I believe this is what Condoleezza Rice’s NSA-sharing service, Dropbox, does already.

Occasionally, Match will insist that a particular song is a duplicate, but searching through iTunes will not reveal any same- (or similar-) named track that this song might be duplicating. Naturally, iTunes does not offer to show the other file, so you have to decide whether you trust iTunes’s judgement (recommendation: don’t).