When I click a number to play in iTunes, I get a pop-up that says "cannot find original file", Please help.

The above problem goes for all my more then 2000 songs. I get the option to search but that doesn't give any results as well.
I upgraded to Lion 2 weeks ago.
Any ideas?

Here are typical layouts for the iTunes folders:
If you have upgraded from version 8 (or earlier) to iTunes 9 (or later) at some point, then your media folder (everything inside the red outline) may still be called iTunes Music instead of iTunes Media. The extra Music folder inside the media folder is used if you have allowed iTunes to Upgrade to iTunes Media Organization (iTunes 9) or used File > Library > Organize Library > Reorganize files in the folder "<Media Folder>" (iTunes 10). Depending on your choices for Keep iTunes Media folder organized and Copy files to iTunes Media folder when adding to library plus a little bug in which one build changed the name of the file storing the choice of layout it is quite easy for some of your files to be organized according to one layout and some the other.
It is possible that in the upgrade to Lion iTunes has been installed with the current default options while your library is based on an older structure. Use Get Info. on a missing track, click cancel when asked to locate it and look at the path given on the summary tab. Now look for the actual file with Finder. Post both paths back here and we can try to make sense of the problem.
tt2

Similar Messages

Maybe you are looking for