Three essential iTunes Match troubleshooting tips

This is Apple's go-to all-purpose troubleshooting fix. If anything is not working with iTunes Match, this should be the first thing you try. In my case, after at first subscribing to iTunes Match, I had several dozen songs listed as Error. Afterwards selecting the Update command, the songs were successfully matched. To tell the truth, I had to select the command three or four times earlier everything possible was matched; I nevertheless have two songs that are stuck with an Error status.

Rule worked for me

While this technique has as a rule worked for me, I had one instance where clicking Download icons led to 5099 error messages. The message recommended that I check to see if I had an active network connection. Quitting and relaunching iTunes did not help. Neither did selecting Update iTunes Match. Nevertheless, turning iTunes Match off and back on again did the trick.

You may run into trouble that cannot be fixed by any of the above techniques. Unfortunately, there is not much you can do as late as this. Currently, Apple provides no additional tools for managing iTunes Match.

What can I do to force iTunes to match in other words than upload these songs? As far as I can tell, there is nothing I can do--other than wait. A Macworld article confirms that others are seeing this same glitch. The consensus is that a server error is at fault. In other words, it's a problem in the cloud, not on your Mac; all you can do is hope that Apple will in the end address it.

Similarly, a friend of mine had a problem where, afterwards subscribing to iCloud, most of his songs remained stuck in the "Waiting" status. None of the above-described fixes had any effect. He found several forums threads describing the same symptom--with no solution. In such a case, afterwards over a day of frustration, the problem fixed itself. Follow-up postings online indicated the remedy was happening at about the same time to all who were affected. Again, the implication is that this was a server error that Apple had resolved.

For other questions you may have about problems with iTunes Match, I recommend Apple's Troubleshooting iTunes Match and Macworld's iTunes Match: What you need to know.