Well, thanks to #pfsense I have this working now. Adding this for others and mainly myself, so I can re-do this at a later point :)
First I created a static dhcp lease for the machine that I wanted to use a certain WAN interface:
(if you run into trouble with the machine not using the static lease ip, make sure all other dynamic leases for the machine are removed, I had to do that and restart networking for this ubuntu machine for the static lease to go into effect)
[image: 5617cad183a19.png]
Also I selected " Register DHCP static mappings in the DNS Resolver" under Services->DNS Resolvers so I can address this machine with "ubuntu" or "ubuntu.bindibox.net" (my local domain name)
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In Hyper-V, I have created a Virtual Switch attached to my physical WAN connection:
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and pfSense uses this for WAN aswell.
I shut down the pfSense VM, and gave it more network adapters in the VM settings:
[image: 5617cc443c492.png]
and attached all of them to the vswitch that I mentioned above:
[image: 5617cc7619548.png]
then under Interfaces->Assign in pfSense, I assigned the newly attached WAN interfaces and named them like so (i plan to name them wanubuntu, wanmumble, wanplexmediaserver so its more easier to understand which interface i want to use for which virtual machine):
[image: 5617ccc1eae02.png]
[image: 5617cf82b0b82.png]
Then under Firewall->Rules, under LAN tab I created a new rule:
[image: 5617cd2a3eab1.png]
and put it above the other rules by selecting the other rules and pressing "move other rules to the end":
[image: 5617cd9b45716.png]
You might want to remove gateway monitoring for all but one of them, under System->Routing by editing the gateways listed in there, for this very technical reason:
< monitus> apinger being a pile of poop and not working correctly with multi wan
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Voila, it works!
First wget is before applying the previous rule we created, second wget is after the rule is applied:
[image: 5617bb22c7a6a.png]