Hosting 2 webserver machines with iis10

cn flag

I have an interesting problem.

Basically I'm hosting 2 webserver machines (Production and development) on the same IP address. Each one is running IIS10 on Windows Server 2019 and each has it's own unique SSL certificate installed.

The Production server is using port 443 in it's bindings and can receive incoming webhook requests.

The testing server I can't use 443. So I designated it with port 444 in the bindings instead. Since the port is 444, I have to include the port number in the URL. webhook requests don't arrive.

Has anyone encountered this? Is there any kind of work around?


markymarc1981 avatar
cn flag
's actually 2 different machines. Each machine is running IIS 10 on Windows Server 2019. Each machine has it's own SSL cert with unique domain name. The problem is that both machines need port 443 otherwise I have to specify the port in the url which will not work. Also, I can only forward 443 to one machine in the router port forwarding These machines are running a site that is listening for incoming webhook requests
Nikita Kipriyanov avatar
za flag
Please, edit your question and move your comment into it.
za flag

"Production" and "development" could be considered as two different web sites which happened to run the same application. This means, your problem boils down to running several different web sites with SSL on the same IP address (and port).

This problem is the valid use case for the reverse HTTP proxy.

Give your sites different names (which will be used to refer to them by the third parties). For example, one could be called and the other This is enough for the proxy to be able to distingush and route requests to appropriate server.

For running both sites with SSL, you need your reverse proxy to support SNI and install all certificates with private keys onto it. Also you configure request routing on a proxy such as gets routed to production server and the to another server. Then you have to forward port TCP 443 to your proxy.

Your software choices include at least Caddy, Nginx, Apache; there are more. I wouldn't be surprised if IIS itself could do reverse proxying; in this case you may forward port 443 directly to the production server, which runs production site and also configure it to proxy development site to the other server. (IIS supports SNI since version 8.0.)

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