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Publishing two IIS webservers, One External IP

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This question is similar to one I asked previously, but this time the situation is a bit different.
http://community.spiceworks.com/topic/318373-subdomains-directing-to-different-web-servers-behind-single-public-ip-address

That time using different ports ended up being the best scenario.

This time we have two Server 2012 servers in an AD SSO hybrid Office365 domain. Because MS is lame, we had to build a second server for ADFS Synchronization and for RDS. So we have IIS on the DC for SSO authentication and we have IIS on the second server for RDS.

(In case anyone cares, we were originally going to try and do the hybrid setup with just one server, but we didn't find out until after ADFS was installed and linked to MS Online services that the sync tool can not run on a dc and must run on a server. Hence the ADFS url on the DC. Lame. That's why this setup is a little wonky.)

What's the best way to publish the RDS site externally without playing hookie with ports and subdomains? Ideally, I want connect.domain.com/adfs to work as it currently does for SSO, and I want connect.domain.com (with no subfolder) to redirect to /RDWeb on the second server.

Host headers won't work (at least not easily) because the second site is hosted on a second server. HTTP redirects in IIS also won't work because the internal redirect url won't resolve for external users.

I have full access to internal and external DNS and IIS on both servers. I'm not a web dev, so any solutions should be pretty detailed :) Thanks!

:EDIT:
What I've decided to try doing for now is install the RDS Gateway and RDS Web Access roles onto the DC (since it's the Connection Broker that causes the pain with ADDS). What I run into with that is that none of my published apps show up on the Web Access on server 1. I assume this is probably because I didn't remove the web access role from server 2? Is this configuration even possible, since the remote apps I need to publish are on server 2?


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