Setting up Subsonic with IIS 8 in Windows Server 2012

Adding WordPress to my server presented some issues with my already installed Subsonic server. Wanting two different sites on the same IP address to share HTTPS capabilities isn’t very easy when you’re playing with both IIS and Jetty (Subsonic’s built in web server). In order to get around this I set up a shell site within IIS that forwards connections to Jetty.

IIS 7/7.5 has limitations around using multiple SSL certifications with multiple sites when they are not a wildcard certificate (being able to run multiple sub-domains under one certificate). IIS 8 has added this feature, and allows sites running completely different domains ( and to operate both with their own SSL certificates.

Instead of getting a wildcard certification (which is much more expensive than a regular certificate), I bought two regular certifications. One points to my main site, the other to the Subsonic server:IIS 8 SSL Certification View

Since Subsonic is not hosted within IIS, but within Jetty, I added some URL rewriting to the rules:


The rule simply takes anything that comes into the domain and forwards it to another server within the internal network. This allows the URL to stay consistent with the user, all they see is IIS decrypts the steam and sends it to another server which hosts Subsonic. Since the certificate is assigned per site instead of per IP now, both sites can have valid SSL verification within the browser even though there is no wildcard SSL certificate in place!

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