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Actually it might have been Tiger plain and simple I can't really remember since I just started doing some major icon overhauling recently. But under Panther you used to always have to wait a while for the sidebar to update the icon if ever. Not to mention sometimes icons wouldn't be replaced just for random reasons and junk... anyway that has all changed with Tiger! I didn't even notice my lack of headache until recently... but... I'm very much enjoying things.
There's one icon problem that Tiger didn't fix for me. If I have my icons arranged in a certain way in a window and I edit and save any of those files, its icon will jump to a random position inside the window breaking the original arrangement.
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