I use TeraTerm to interface with teh old Bport. I use it to send my Gcode file to the Bport.
There is a lot more too it than just settings. Sometimes you have to reset the connection and force the BOSSeditor to end and restart a new session.
You also need to have the dials on the Bport set to the right settings to transfer. Otherwise you are talking to a deaf machine. You need to check the status of the terminal to make sure you are getting a response from teh Bport to initiate the 'handshake' to pass the information.
I have never tried through the BobCAD software to send files. Only create Gcode and send the files with other software.