After I turned iTunes Match on and waited through the process of getting my music into the cloud, I was pretty happy with the result. Only about thirty songs of mine didn’t send for one reason or another. But with just a little tweaking, I got most of the rest of them to go, and it took much less time for me than choosing Store > Update iTunes Match. Here’s how you can attempt to individually force songs into the cloud (and how to tell which ones didn’t go in the first place and why!).

To see what didn’t make the cut, go into iTunes. You should have a new column when you’re in list view that looks like this:

If an icon appears in that column next to a song, it wasn’t added to iTunes Match. As you may know, you can click the column headers to sort by them, so do that to gather all of your rejects in one section. Luckily for me—since I’m not so great at deciphering what those icons might represent—Apple’s put up an article with explanations. I mean, yeah, now that I see what they’re supposed to mean, I understand. I guess. 

Those icons are clickable within iTunes, too, and doing so gives you another way to get an explanation for why your stuff wasn’t sent to iCloud.

If you prefer, you can add still another column in iTunes, which I think makes things much clearer. So right-click on the column headers to show the list of possibilities, and toggle on the “iCloud Status” column.

Right-click anywhere on here…

…to bring up this menu.

After you do that, it’s pretty easy to see what the problem is for each particular item.

You can then select all of the songs that can be sent to iTunes Match but didn’t go (such as, for example, the ones that reported errors), right-click on them, and choose “Add to iCloud.”

Neat, huh? I think I’m finally starting to get the hang of this. Give me some more time and a lot of coffee laced with something alcoholic, and I’ll be good to go on iTunes Match. Or just good to go, anyway.