Can't access IIS website inside a VM via HTTPS

0

I'm running Win10 through Parallels and trying to access a website in IIS from a browser outside the VM.

I've added an entry to my hosts file which maps the VM's IP address to "windows", and I can browse to the IIS welcome page using http://windows/.

But I'm unable to navigate to a website under the IIS root.

Furthermore, the website runs on a self-signed SSL certificate (having used this guide) and the website redirects HTTP traffic to the secure URL.

I think this HTTP redirection is causing me problems but I don't know what to change. For example, if I browse to http://windows/mywebsite/ the page never gets there. Instead the browser displays "This page isn't redirecting properly". So the request is getting to the destination and triggering the redirect logic.

And if I try to browse to https://windows/mywebsite/ then I get a 404 (Not Found) response.

The Windows Firewall has an "allow" for port 443 and all columns say "Any" except for the "Program" which says "System" (although I've added an entry which contains "Any" in this field... but no difference).

Can anyone explain what I need to do to enable https browsing from outside the VM and why I'm currently getting a 404 response?

awj

Posted 2016-01-04T20:14:51.373

Reputation: 103

Is IIS bound to port 443? – heavyd – 2016-01-04T20:28:47.443

@heavyd Yes - I can see in IIS (in the right-hand column "Browse Website") that it says "Browse localhost on *:443 (https)". – awj – 2016-01-04T20:31:17.877

If you're getting an actual 404 error, then the web server is answering (and telling you it can't find the file/resource requested). Can you access it via Localhost (ie: http://localhost) from the machine hosting IIS (the VM in this case)? Can you create and access a basic HTTP (no certificates) site from the local host? If not, then it's a IIS/website configuration issue, not a firewall/connection issue. – Ƭᴇcʜιᴇ007 – 2016-01-04T20:42:49.153

@Ƭᴇcʜιᴇ007 Yes, I can access the site from within the VM. The URL is not the problem. As regards your second question, I'm not sure what you mean but I can access the IIS welcome page at the IIS root. – awj – 2016-01-05T07:54:32.847

No answers