I use TMG as a reverse proxy to redirect SSL traffic based on URL using a third party wildcard certificate. I've configured this over other devices (namely unsecured HTTP pages for internal devices, NAS, UPS, etc) and other Windows products. When configured with WHS (installed the WHS self-signed certificate on the TMG) and can access the WHS remote access site and it renders the home page, but not the Media Library portal and when I access the Share Folders it returns an error.
There is nothing in the WHS event log and TMG is reporting Alllowed. I've also disabled the HTTP filter rules that can trap extended traffic.
Can get the media library and transcoding player to run by forwarding the original host header, but does not resolve the browser file manager. Note: the NetBIOS host name is used as that is what WHS uses to generate its self-signed certificate.
The last piece of the puzzle (file manager error message) was addressed with Update Rollup for Windows Home Server 2011 (KB2630434) which also addressed a transcoder issue where the aspect ratio was incorrect (rendered as 4:3 when content was 16:9).
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