On our FarCry install it appears that when I delete files from the Content > Media & Categories > Document Library that there is nothing in the way of deleting files already associated with content. I did see Justin state elsewhere that this is suppose to be default behavior.
Is there anything obvious that could be getting in the way? I've tried looking through our custom side of things and have come up empty so far. Digging through the core side of things it appears that images go through a block of code blocking images in use, dmFile.cfc doesn't include it's own delete and appears to go through a more generic function
Anyway, I assume there's something wacky in our install or configuration. I haven't been able to find anything custom either, so I'm unsure where to look right now.