It could be that a php error is preventing the second file from uploading. add the following code at line 1 to turn on error reporting:
are you using 2 separate file uploads?
For the File Name, go to the bindings panel and expand the WA Uploaded Files (File Field) Binding group.
If you have 2 separate uploads there will be a binding group for each file field.
This binding group will contain a binding called Server File Name, this binding can be added to the email message to show the name of the uploaded file.
If you wish to attach the uploaded file, edit the Universal Email server behavior. On the Attachments section add a new attachment and select the enter value option. click the lightning bolt to open the bindings panel and expand the first WA Uploaded Files binding group. Select the Server Directory binding and copy the code for the server directory, then select the server file name binding. past the server directory code in front of the server file name code.
Repeat this for the second file upload.
send a copy of your page so I can see how the upload is configured.