why does Itunes say it can't find the original file for a particular song?

Basically, this means that the files are no longer located where iTunes thinks they are. You need to find these files on your hard drive and add them back into your iTunes library.

CG

My itunes 7.7.1 on my Macbook has also been losing connection to it's original files. "original file not found. Do you want to locate it?"... I relocated the songs, (3 hours!) had a 100% connected music library, stopped, put the computer in sleep, and the next morning, woke the computer to find even more links broken than before! Different songs, and things that I had reloaded from CD the night before, even. I have made a new music library. I have reloaded from CD. Of course, I have backed up to CD and/or external drive. It seemed my purchased songs were the first to DISAPPEAR and I had to rebuy.(Nice scam in the bug?) I am now convinced this a HUGE BUG in 7.7.1. and possibly the previous version or two. I reloaded my original iTunes 7.4.2 from my orignal software that came with the computer, and everything is fine. - in fact, everything I've reloaded 3 and 4 times showed up again!(except my purchases) Now My Ipod 8GB won't work because it wants the newest software on the I-Pod. very frustrating not to see an acknowledgement from Apple that this is happening.

sheri 0713 wrote:
Of course, I have backed up to CD and/or external drive.

I'm wondering if you're attempting to maintain your library on your external HDD? If iTunes has been directed to use a location on your external hard drive as your iTunes Music Folder location (you can check this in iTunes > Preferences > Advanced tab) you MUST ensure that the hard drive is connected to the computer and mounted in the Finder prior to launching iTunes. If it isn't, it can cause this error to appear. This is probably one of the most common reasons this error begins to appear.

It seemed my purchased songs were the first to DISAPPEAR and I had to rebuy.(Nice scam in the bug?)

So... why not restore them from your backup? If, for some reason, this wasn't an option, you could have also recovered them from any iPod or iPhone they were currently synced to ( http://support.apple.com/kb/HT1848), or, you can also email iTunes Store support and request a "regrant," which is a once-per-account exception they might be able to offer you and allow you to download missing purchases again.

I am now convinced this a HUGE BUG in 7.7.1. and possibly the previous version or two.

I'm not so sure... I've never run across this particular error (my library is stored on my internal hard drive, but copied to an external for backup purposes with an application other than iTunes or Finder. I don't think Apple will provide acknowledgment to issues experienced only by very small numbers of people... I'm one of those, perhaps foolish, individuals who allows my computer to download updates immediately, rather than waiting for fear of problems, and again, I've never had this error.

CG

Thanks for the ideas....I had most of that covered as I search forums for solutions regularly and my husband is an Apple IT guy...I am not running off an external drive... that's just my new backup. The library I use is on my Macbook. I had already created a new folder on my hard drive as my music location before this last round of losing connections to my songs as you mentioned...so that didn't fix it. Second, I was caught off guard by the disappearing songs, and so NOW, hindsight has kicked in, and i'm making 2 backups immediately as I buy stuff. As far as reloading from another device, I lost everything i purchased before I had the ipod and hadn't made CDs yet; so the songs were just on my computer. no backup. doh. Now I know better."Operator error" as we say. Curiously, we have two Macbook Pros of different model years and and I-Mac in the house, and only my MacBook is having this problem. Thanks again for the response, though. I'll rely more heavily on my backups.