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In your global options and storage options try making sure your paths are forward slashes like so
X:/dir/subdir/web/data
That is both global and storage paths in admin. As far as permissions you need to set both your uploads and data directories to READ WRITE EXECUTE permissions based on our install instructions for things to work correctly. You want GUESTS IWAM and IUSER accounts to have these priviledges.
I dont beleive animated gifs can have thumbnails created for them to my knowledge
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