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Perhaps I can't find an option, but iTunes doesn't seem to monitor folders for changes on Windows. Is this possible to do?

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up vote 3 down vote accepted

iTunes doesn't monitor folders the same why Media Player does, however you can let iTunes manage your music in which case it will apply any changes to these folders automatically.

However when you Add a Folder to iTunes it will add all the music in that folder and not create duplicates. When manage my music is on it will also organize it correctly in the iTunes folder, if off it will just add the songs to the library.

There is also a third party application called Folder Watch that can do it for you.

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since you're using iTunes in Windows, iTunes Folder Watch may be for you.

and here's a tutorial How to Automatically Update Your iTunes Library?

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Why is it that we always give the same or similar answers? – BinaryMisfit Sep 7 '09 at 20:44
great minds? LOL – Molly7244 Sep 7 '09 at 20:51
Let's say that's it and leave it at that shall we :) PS: Fools never differ – BinaryMisfit Sep 7 '09 at 23:01

Also, if you simple go File -> Add Folder to Library, it will re-scan the folder and add anything new.

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ITunes Libarary Update will allow you to synchronize your iTunes Library (even though it is a getting a little old, it still works fine with iTunes 9. If you want to keep it in Synch you can follow this tutorial. The main problem with adding a folder to iTunes is that it doesn't remove orphaned (deleted) entries.

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