In my virtualbox I had Whonix Gateway 8.0 (yes almost 3 years old) and Windows 8 as Workstation. I have since imported the latest whonix gateway 184.108.40.206 as a new VM. My issue is I have a program that does multiple connections to the internet and with the old 8.0 gateway I monitor the connections coming out of the gateway and it goes to 3 tor entry nodes properly doing a stream isolation BUT in Whonix Gateway 13 it only goes to 1 tor entry node.
I have done the better protection section of the guide like I did on gateway 8.0 and I am not sure what I am doing wrong now. https://www.whonix.org/wiki/Stream_Isolation#Better_Protection