We have this question on Super User: Drupal image. Files storing to wrong place. Imagecache?
It's off-topic for Super User, for sure. However, I'm not sure where to refer the user to. He is obviously in a webmaster position, but he is mostly asking about why something doesn't work correctly in drupal. I checked the FAQ, but I lack knowledge on the subject to judge if it's matching or not.
Is this question on-topic on this site?