Trouble with adding music to iTunes?

I've spent the last few days retagging (with MusicMatch 10's SuperTagging feature. Works really well!) all of my music so that I could add it all to iTunes. I like iTunes. Very well done for a media organizer, and I'm pretty anal about my organization. So after all of this was done, I started adding music to my iTunes library. Took a while, but it was finally done and I was happy. For a moment anyways, I started to notice that some of my MP3's were missing from iTunes. I tried to drag those individual directories onto iTunes and nothing helped. No error message. Just nothing happened. Baffled, I did some research online and found that this wasn't actually that common of a problem. A few people had this problem but no real answers about why or how to fix it.

Here is what I have noticed about this weird 'bug'. I've seen some suggestions that your music was tagged in an improper format and that's what caused this. This is impossible because ALL of my music has been tagged with MusicMatch 10 now and not all my files are having problems. So I decided to erase my entire iTunes library and start over. I decided to take each individual album and start dragging them one at a time into iTunes. What I realized is that downloaded music, or music I more recently ripped to my computer added fine, but I found that a large quantity of my albums that I had ripped about 3 or 4 years ago (using whatever MusicMatch was newest then) were the problem files. Here's how I fixed it. It's really simple, but it takes some time.

Download CDex and install it. You might want to fiddle with some of the settings as their default is 128Kbs.

When that's all installed. Find out which items are not being added to iTunes and move those folders to a temporary folder.

In CDex go to the Convert menu and click Re-Encode existing compressed audio. This will give you a few options, browse for the folder you saved all your delinquent albums on the top and click the Search SubFolders check mark and make sure the 'keep existing directory structure' is checked. Then Click Select All and let it go.

CDex is a great program that re-encodes your MP3s with whatever codec you might want to use while still keeping all of your tag information. It uses LAME by default which is fine and dandy by iTunes standards. If you have a lot of files, you might want to just leave your computer going for a while. I've found it takes about 15-20 seconds per song to encode.

When it's done doing it's thing, just find the folder it saved all your music to (You should have set this in your options, but by default it goes to your My Music folder) and move the files back into your music collection.

Try and add these files into iTunes now. If it works, GREAT! You can go ahead and delete that temp directory with all the old MP3's in it. If it doesn't work, I don't know what to tell you. This worked for me. Hope this helped anyone!