Can't delete song files

Running iTunes 9.1 on Windows XP Home Edition 2002, SP3. Almost every time I go to delete a song, it no longer gives me the option to delete the file so I'm not clearing any space on my drive. It does this less often for apps, but still does it. Is there an option I turned off by accident? Is this just a bug? Thanks for the help.

I had the same problem. I found many duplicates on my pc after moving files to an external hard drive. Some duplicates existed before this move but I did not worry about them. So, after a while my children were running out of space on their ipods so I used the "Show Duplicates" feature and deleted "the .....ing duplicates". Now my children tell me a great deal of their purchased music is missing and they are very annoyed. I told them that I thought Apple/iTunes spoke English and that Duplicate means just that, A Duplicate. This is extremely annoying. It seems like such a common sense fubar thing which is contrary to the awesome quality of the itunes/ipod in general. How do I get the songs we already *payed for* back on our computer? Or, are we screwed and in a spot where we must repurchase this music? Honestly, this is something I expect from microsoft, not Apple.

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Currently if I want to delete any songs from my HDD I have to:
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○ Click "Show in Windows Eplorer".
○ Delete the file.
○ Delete song in iTunes library.
◙ And repeat it all if there are more than one song I need to delete.
Is there any way to delete files from iTunes directly?

Stuwawah wrote:
You can but in order to be able to do it directly from iTunes, the song/songs need to be store in the "iTunes folder" in your media directory or the Default folder to chose Under:
** Preferences -> Advanced -> Itunes Media folder location
That is not accurate.
I do not keep my media in the iTunes folder because I personally cannot stand the way iTunes manages the folders.
I am able to delete media from my computer via iTunes by simply selecting delete and then selecting the option to let iTunes remove it from the drive.

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After downloading ver 7.0.2 I can't delete songs from my hard-drive by deleting them in iTunes.
There's supposed to be a dialogue(sp?) box that shows up when you delete a song in the main library (not in playlists), that asks you if you want to permanantly delete a file (song, movie, etc), or if you only want to delete it from the iTunes list.
It's not showing up for me, so I have to seek out the folder and delete the song manually in Windows.
I'd get this problem occasionaly in the older versions, but usually a restart of the program, or in worse cases, rebooting the computer would solve the problem, but not this time.
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I tried the following fix, and it didn't work..
Is anyone else having this problem after upgrading to 7.0.2?
I'm sure I didn't check the box in the delete dialog that says "do not show this again"
I've also tried hitting the shift key when deleting.. still no luck.
HELP!!
Resetting the iTunes Preference Files:
-- Quit iTunes
-- Delete C:\Documents and Settings\<your username>\Application Data\Apple Computer\iTunes\iTunes.pref
-- Delete C:\Documents and Settings\<your username>\Local Settings\Application Data\Apple Computer Inc\iTunes.pref
You may need to enable 'Show Hidden Files/Folders' in Windows Explorer==>Tools menu==>Folder Options==>’View’ tab before you can see the Application Data & Local Settings folders.
This will force iTunes to run the setup assistance the next time you open it. You'll have to go back and re-set any preferences you want changed from the iTunes default. When you restart iTunes, it will perform its initial startup process. Do not let iTunes search for your music files. The old library is still there and iTunes will see it after it gets past the initial dialog screens.

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Can't delete song files

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