Switching backup drives

Until recently, all my iTunes songs went directly into a file on an external hard drive.  That
hard drive was quite small, so I recently copied my 27,000 songs onto a new, larger backup drive.
All new additions have been dedicated to that new drive.
However, I cannot play any "pre-change" songs without having the old drive hooked up, too.
If I only have the new drive hooked, I get the "question mark / cannot locate" on all older
songs.  Post-change songs play fine. All songs are clearly in the new drive.  If I go into the new drive and click on the "unlocatable" song, it opens and plays as if it's a new addition.  So, when I hookup the old drive, too, I now have duplicates.
What am I doing wrong?

I am guessing you just have media on the new drive, not your whole iTunes library (all the library files and folders in an iTunes folder).
What are the iTunes library files? - http://support.apple.com/kb/HT1660
More on iTunes library files and what they do - http://en.wikipedia.org/wiki/ITunes#Media_management
What are all those iTunes files? - http://www.macworld.com/article/139974/2009/04/itunes_files.html
iTunes does not like it when you move media to a new location, especially not to another drive.  You have to let it do it so it can keep track of things.
Solutions:
1) Connect both drives.  Use iTunes preferences to change the location of the media folder and let iTunes consolidate media to the new drive.  iTunes 10 for Mac: Consolidate your iTunes library - http://support.apple.com/kb/PH990 and iTunes for Mac: Moving your iTunes Media folder - http://support.apple.com/kb/HT1449
2) Assuming the folder structure is pretty much identical to the one on the old drive, you can: A) Find one song on the new drive and hopefully iTunes can find the others (say yes when it asks if you want it to do this), or B) Give the new drive the exact same name as the old one and hope it tricks iTunes into thinking it is the same drive.
By the way, this is not a "backup drive".  A backup is a second copy you keep for when your main drive fails.  This drive is being used actively for your primary iTunes use. When this new drive fails you will, of course, lose your whole iTunes collection unless you truly do have a real backup drive.

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    Message was edited by: imaginary_forest

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  • HT201250 I have two external hard drives. One is my Time Machine backup drive.  The other I use for external storage of files (documents, photos, movies, etc).  Can I set Time Machine to backup BOTH my Mac hard drive and my other external hard drive?

    I have two external hard drives. One is my Time Machine backup drive.  The other I use for external storage of files (documents, photos, movies, etc).  Can I set Time Machine to backup BOTH my Mac hard drive and my other external hard drive?

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