Windows Home Server 2011 - Dynamic DNS - Internal IP Problem - Solved
I feel compelled to share this knowledge with the forum as it took me a long time to find it even though it was jumping right out at me in the Google results. Windows Home Server 2011 is an old product, but I still use it.
Windows Home Server has a nifty website that allows remote access to your server with various functions and there is a nice wizard to set it all up. The average user will let uPnP setup port 80 and 443 automatically or you have the option to bypass uPnP and tell WHS that you'll setup your router manually.
The next part of the wizard also allows you to setup a DynDNS domain through Windows Live Domains. You get a *.homeserver.com and an SSL cert to make everything work really nicely. You just set it up via the wizard which configs the ssl cert and WHS is supposed to update live domains with the IP, just like DynDNS with the awesomeness of an SSL cert.
There are many threads where users report that the IP getting sent to Windows Live Domains from WHS is an internal one.
So an nslookup would return the following:
Here are some threads that went no where, also this is known to happen with ClearOS too. There were some on social.microsoft as well. Most of them centered around people spewing out info about "You should check your ports blah blah"
http://forum.pfsense.org/index.php/topic,42812.0.html (thread closed)
I searched high and low and I was considering getting rid of pfsense and trying something else. However the fact that ClearOS had the same issue was discouraging… I didn't want to fall back to a consumer router which worked fine,
I found the solution here: http://homeservershow.com/forums/index.php?/topic/4980-issue-with-rwa-after-switching-to-pfsense-router/
You need to exempt the homeservers internal IP from Squid, somehow squid messes up the DNS update from WHS to Windows Live Domains.
The End, I'm going to sleep.