It seems to be related to the fact that the image file name does not change when the file is uploaded.
The way the page displays the image it just checks to see if the static image file exists "file_exists( 'filename.jpg' )" and if it does it displays it. I upload the same file names every time the user changes their head shot image or company logo. The file names never change, the images are just overwritten every time.
I created a page that changes the name when the file is uploaded and another page that keeps the file name static. The page with the name change updates correctly while the page with the static file name never updates at all unless the client forces a refresh of the page manually (ctrl+F5).
I don't have any idea how to solve this. It seems like a long way around the block to save the file name in the db and have it increment the name every time they upload a file. Not only is it a pain, but it is a waste of db resources.