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Trouble setting up ADFS 2.0 proxy with Office 365

Posted on 2013-02-01
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Last Modified: 2013-02-07
Hello again all,

I'm currently struggling through the process of setting up a hybrid forest with Exchange Online and our on premise Exchange 2010 server.  For our network, we need ADFS for the authentication to our on premise Active Directory.  We have our local domain setup as example.local and we also have our public domain hosted with GoDaddy as example.com for our email, website, etc.

Now I have three Windows 2008 R2 servers in place.  Two of them are running ADFS 2.0, joined to our example.local domain, and configured for NLB with the hostname being adfs.example.com for the cluster (setup on our local DNS server).  The other server has ADFS 2.0 Proxy running on it, is not joined to our domain, has nothing configured on our local DNS server, and our public domain at GoDaddy is setup as adfs.example.com point to it's static IP.

In terms of Office 365, our domain is active under federation.  I have not begun anything with the hybrid Exchange forest yet as I'm trying to get ADFS configured.  During the ADFS proxy configuration wizard, I try to test the connection to adfs.example.com and it is unable to get any connection.

I'm sort of at a loss at how all of this fits together at this point.  I would greatly appreciate any help you guys could shed on this matter.  Thanks!
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Question by:jbcsystech
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by:jbcsystech
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Just a quick follow up with the actual error message I'm receiving.  I'm just trying to test the connection I've setup to adfs.example.com at this point when I receive this.

connection test error message
I have our internal DNS setup (adfs.example.com and adfs.company.local) to point directly to the ADFS NLB IP while our external DNS points to the proxy server's static IP.

Here is the guide I'm trying to follow:
http://pipe2text.com/?page_id=399
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jbcsystech earned 0 total points
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I actually figured out what my problem was (after calling Microsoft support directly).  I needed to enable port 443 for traffic between the ADFS server cluster and my proxy.  Plus open 443 up from the proxy to the extranet.  Check out this link for more information.
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