I tried all combinations, but I went back and played around with it some and found my issue. Apparently after you stop the debugging session System Workbench doesn't automatically remove the terminated connection. So I had more than one connection, which seems to be my problem - and I'm guessing the default .cfg file clears all old connections before it starts.
So for anyone who comes along searching for this, make sure to clear out all old connections shown in the screen cap: