When you make a PDP Toolbox transcript points request, you can now upload multiple files along with your request.
In your PDP Toolbox activities page, open a new Transcript Points Request and scroll down to the "Artifacts" field located in the Post Activity Information box. Here, each time you add a file to your request, another file browse button ought to appear immediately below the last one. Keep adding files and the PDP Toolbox keeps adding an extra file upload option for you. :)
Thanks Madison M. and Nancy M. for your multiple file upload requests!
Jay @ Greenbush