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Upon removing any removable media, Ubuntu doesn't ask if I want to remove the trash folder to free up space. It used to show a dialogue which prompted me to delete the folder. How can I get this functionality back?

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I have never seem this prompt myself, could it only come up if the USB is near full? You can delete the .trash-1000 file manually, just press Alt+H to show the hidden files in the USB and then you will be able to see the trash file and delete it. (Not quite a true answer to your question so it's posted as a comment.) – TrailRider Aug 31 '12 at 0:47

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