File upload will not work in conjunction with the Dreamweaver Insert or Update record server behaviors.
The native Dreamweaver Insert and Update record server behaviors are limited in that they can only except data from a form.
A file field does not send the file as part of the standard POST array, ot is sent to server using the FILES array, the file upload code tells the server to process the FILES array and move the file to the location on your server you specify, then stores the name of the file in a variable named Server File name.
You will need to use the DataAssist Insert and Update record behaviors to store the WA Uplaoded files -> Server File Name in the database, the Dreamweaver Insert and Update behaviors will not allow this.