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Reverse Proxy To Separate Machine Issues

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Background:

 

My WHS domain is located at cloud.bendwyer.net, and it has an SSL certificate for https access. Attempting to access the URL via http redirects to https.

 

Navigating to cloud.bendwyer.net hits my WHS 2012 Essentials box and loads the Remote Web Access site.

 

I also have a separate, dedicated streaming machine running Server 2008 R2 core, with Tomcat 6.0.37 installed, and Subsonic 4.8 running as a webapp within Tomcat (located at /subsonic).

 

I followed Drashna's guide for setting up a reverse proxy in IIS, but instead of using localhost, I used the IP address for the 2008 R2 machine running Tomcat. I also deviated from the guide by setting the URL rewrite rule at the default site level, per this guide.

 

This allows me to access the Subsonic site at cloud.bendwyer.net/subsonic via http OR https, but not without a couple of problems.

 

Problems:

 

I have an SSL cert for this subdomain, so I'd like Subsonic to utilize it. I tried a few different things to redirect http to https for /subsonic, but the best I was able to do was force a 404 page when accessed via http. This is not really ideal - the Remote Web Access site is able to redirect to an https connection gracefully - I'd like to do the same for Subsonic.

 

Randomly timed, but commonly occurring 502.3 errors when browsing the /subsonic site. The detailed error reads: 502.3 - Bad Gateway - The server returned an invalid or unrecognized response. I have absolutely no idea what is causing this, much less how to even begin go about fixing it.

 

The /subsonic site is down right now while I do some maintenance on the corresponding server, but it should be back up later today.

 

Any advice would be greatly appreciated. Thanks!

 

-Ben


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