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Windows Server 2016, IIS 10

I'm trying to setup a zero downtime code promotion environment and using a server farm on the same server to do this per some other articles I've found as an example. I'm a developer, not a Windows Admin, so I'm struggling a bit.

I've gotten this to work for http requests, but not for https requests...those result in 404 errors.

The image below is what I'm trying to achieve and what I have in my applicationHost.config file. I've read some posts related to ARR Proxy config, SSL Offloading, SSL Certificate binding, etc...but these aspects have me confused.

What am I missing above what I have outlined in my image? Desired Architecture Design

crichavin
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  • Enable FRT and then you can troubleshoot further on your own, https://docs.microsoft.com/en-us/iis/extensions/url-rewrite-module/using-failed-request-tracing-to-trace-rewrite-rules – Lex Li Sep 18 '20 at 20:58
  • @LexLi thanks. I did that and found another issue I can't figure out. I got it working with https. And I can confirm it is reading from site-a, then site-b, so ARR seems to be working. But, I had an original site, just called site, which had the bindings for site.com on 80 and 443. I figured I could stop that site because the rewrite rules (at the server level) should be routing the traffic to the server farm and bypassing the original site. But then I started getting 404 errors. It seem like it is using the bindings in the original site, then the rewrite rules are routing to the farm???? – crichavin Sep 19 '20 at 01:01
  • Correct. You need at least one site on ARR IIS so that Windows knows how to receive incoming HTTP requests. – Lex Li Sep 19 '20 at 01:54
  • @LexLi I have several other sites on this server. But isn't the server level URL Rewrite going to be that which first receives the request, then routes it past any site and directly to the server farm? – crichavin Sep 20 '20 at 02:04

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