I can't seem to get the watermark to apply to any of the photos. I set it to apply on image upload, it didn't appear. I then attempted to manually apply it to each of the photos that I uploaded afterwards through the admin section twice and still no watermark.
Could it have something to do with using WordPress Network/Multisite? It's the only thing I can think of.
Here's one of the images: http://chicagophoenix.com/wp-content/blogs.dir/2/wppa/16.jpg
It was supposed to have this watermark applied both during upload and twice after upload: http://chicagophoenix.com/wp-content/blogs.dir/2/wppa/watermarks/cplogo-watermark.png