ITunes won't copy music files to Media folder when songs are dragged

I am trying add songs from my external hard drive to my iTunes Library.
I have the following options checked:
"Keep iTunes Media folder organized."
"Copy files to iTunes Media folder when adding to library."
In the past, I could just drag files from my hard drive into the iTunes song list and add them to the library. iTunes would successfully make a copy of the file to the iTunes Media folder so that I could disconnect the hard drive and still play the songs.
Suddenly, this no longer works. iTunes won't make a copy of the file anymore. It won't even make a copy of files located on my desktop.
I found a workaround -- copy the files from my hard drive to the desktop. Then I have to go to File > Add to Library in order for it to work.
It's an extra step, but it was VERY annoying to have to figure out.
So my question -- Is this an iTunes bug or some kind of deliberate attempt at making it hard to use files not purchased through iTunes?
I noticed this on one of the Apple support pages (my emphasis):
Copying music to and keeping the iTunes Media folder organized
You can select these options on the Advanced pane of iTunes preferences:
"Keep iTunes Media folder organized." Learn more about how iTunes 9 and later organizes your media.
"Copy files to iTunes Media folder when adding to library." Select this option to store all your media files in the iTunes Media folder. Since it's all in one location, you can easily transfer or back up your media. When you purchase or import media into iTunes from a CD, it's automatically added to your iTunes Media folder. If you add media to iTunes another way (choosing "Add to library" from the File menu or by dragging an MP3 file into iTunes), it might not be added to your iTunes Media folder.
Well, why the heck not??

I have posted so many issues to APPLE on the staggering lack of basic functionality with itunes and each time they keep deleting it.
Automatically Addd feature does not work consistently if the library is on NAS or a drive not on the same bok as the Mac, iMac or PC.
iTuns will hang if you have the finder window open and the recently added playlist open
itunes will not add files automatically if more than three phases of adding folders to the automatically add to itune folder is refreshed
Once could even jump to the conclusion that the software testing and Quality Control in the iTunes development team had missed out whole chunks of tsting OR that the test designers wrote such basic test scripts which did not replicate real world useage.

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In recent years, after a couple of experiences filled with much tribulation, I have never checked either "Keep iTunes folder media organised" nor "Copy files to iTunes media folder when adding to library" under its Preferences, whenever I have been forced to use this accursed application.
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ITunes won't copy music files to Media folder when songs are dragged

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