
Why is DFP changing this when most webservers are going to recognize image.jpg and image.JPG as two separate files?

You can insert the image name using the bindings created by Digital File Pro for the Server File Name to insert the correct name. Uploading the file or copying it over to the correct upload directory is causing the .JPG to be converted to lowercase. Unfortunately the process cannot be changed, so the way the name is stored in the database has to be changed instead.