Hi,
I uploaded an image to a project. The Image was then changed but wasn't renamed. When I came to upload it the image uploaded as I would expect. The only issue was that is associated with the old image and not the new one I had uploaded.
I needed to rename the file for the system to associate to the correct image. I think there should be a disclaimer when uploading an image with the same name as this set our project back 1 week as the old information was being worked on.