The upload file server behavior is not going to work with repeated elements in a form. If the file fields will have dynamic names then you will need to account for this by using the dynamic names in the upload server behavior. There needs to be a File Upload server behavior for each of the file fields that will be in the form. You would want the uploads to occur before the inserts do. Then in the inserts you would need to make use of the upload bindings and the server file name.