I have a physical machine that is hosting a IIS Default Web Site. The IP that has a domain irrelevant to my network in the physical machine. Something like some.irrelevant.com that has a Let's Encrypt cert bounded to the 443 port.
I am using ARR/Url Rewrite/Server Farm to route traffic from Default Web Site to VMs that exists locally. The server farm is called farm.domain.com.
The VMs do not have public facing IPs and are being routed locally using hostnames that are defined in the host files on the physical machine.
I created self signed certs in the VM and bound them to the VM's Default Web Site's 443 port. It is bound to vm.domain.com. It looks like the connection if fine when hitting it from the physical machine.
When I try to hit it via ARR like so it works fine.
- HTTPS -> Default Web Site (Physical Machine) -> ARR/Url Rewrite -> HTTP Server Farm VM Server
However when I try to hit it via ARR in the HTTPS scheme I get a 404.
- HTTPS -> Default Web Site (Physical Machine) -> ARR/Url Rewrite -> HTTPS Server Farm VM Server
I'm trying to find ways to figure out what's going on. Any suggestions will be appreciated.