Just about everyone that uses iTunes has a hella hard time keeping their music files organized. This is a shame because (a) it’s actually pretty simple and (b) it is a colossal pain in the ass to move your library if it’s not organized correctly. (Note that I’m talking about the organization of your actual music files and not the appropriate tagging and categorization of your music library.) The bummer of the thing is that the folks at Apple unwittingly made this more complicated and difficult by trying to make it simple and easy. It happens. Trust me. I have been building software for just over a decade now and it happens all.the.time. Don’t get mad at Apple for this one. Let’s just fix it.

First I’ll tell you what you need to do, and then I’ll explain why.


iTunesIn the iTunes Edit menu go to the Preferences option.
Click on the Advanced tab.
It opens to the General tab.
Your iTunes Music folder location should be something like:

C:\Documents and Settings\David\My Documents\My Music

The David in that directory path should be your name instead of mine. (If your name is David, you’re golden.)

Special Note: If you want to get really crafty, and I do advise this, you should store all of your music on an external hard drive which is always connected to your computer. Or at least one that is always connected to your computer whenever you want to synchronize an iPod or iPhone and / or listen to music.

Underneath that file path are two checkboxes:
Keep iTunes Music folder organized and
Copy files to iTunes Music folder when adding to library
Both of these checkboxes should be checked.

The big trick here is the difference between MOVE and COPY. Most people don’t really grasp the difference between those two concepts. When you MOVE a file, you are taking it from one location and putting it in another. If you MOVE the orange juice from the fridge to the counter, the orange juice is no longer in the fridge, right? Now it’s on the counter. Its existence in the refrigerator has ended and it has a new life on the counter, presumably soon in a glass and then in your stomach. If you COPY the orange juice from the fridge to the counter — aside from having some amazing Christ-like abilities — there would now be two cartons of orange juice: one on the counter and the original in the fridge. You can’t do this with cartons of OJ, but a computer can do it with files. (If you can, again, that’s some amazing shit right there and you should call the Pentagon because they really would love to talk to you.)

So, say you have 100 songs in C:\Stuff or D:\music (or on a thumbdrive or an external hdd or something) … when you ‘import’ into iTunes, it will not MOVE the files … it will (literally) make a copy in the location you have specified as the “iTunes Music folder location”.

Pretty much everyone I know has two copies (at least) of every song in their library somewhere on their computer because of this. They think that they are MOVING their music files when really they are COPYING them.

The trick is to create a folder inside the location and to use that as your “staging” location. And you need to name this something that will never ever be the name of a band or an album, so, hypothetically, you’d have:

C:\Documents and Settings\David\My Documents\My Music\iTunesStaging

Any time you are importing a CD or buying from iTunes, it’s going to go into the right place by default. But if you are copying files from someone else’s machine (or a thumbdrive, or from LimeWire or something), you put them into that staging location first, then use the iTunes File->Add File to Library option to import the file from the staging folder … which will MOVE (instead of COPY) the file to the right directory in your music folder.

Here’s the kicker:

It will MOVE instead of COPY because — since the staging folder is INSIDE your music location — it thinks it’s just rearranging things instead of copying or importing.

Hopefully that all made sense to you.

2024-01-16: Dead links in this post have been removed and/or updated.