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which are then automatically imported into my music library (itunes).
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Here lies the problem.
Why does it "automatically" import the files anyway?
Can you switch this setting off?
What happens when there are .mp3 files present on your disc that you don 't want in itunes?
It sounds that with this "automatic" import,Itunes is saving the path to the .mp3 files at the location they are when it discovers them.
If you then move them,or delete them,or rename them,Itunes can't find them anymore.
When you let Itunes "convert" to .mp3(a file that is already .mp3 anyway),Itunes is probally really copying the files to a new location,with the path to those files being default,
and at this location you never move,delete,or rename them,so all is good.
This sounds more like bad scripting(a bug)within the "automatic" feature in the Itunes application,rather than a mistake that you're making.
One would think that script running for "automatic import" would....
#search for non duplicate .mp3 files
#if found,copy to default database
#update default playerlist
#exit and resume search
It isn't doing this.