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SBS 2011 - TS Gateway / Remote Desktop Certificate Mismatch Failure

Posted on 2012-04-04
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Last Modified: 2012-04-05
Please bear with me as I was recently supporting a SBS server already setup. What I do know is that company is using mail.contoso.com certificate from GoDaddy that is used for seemingly all of there certificates against the server. Remote.contoso.com was issued by server-CA for the Terminal Gateway. Everything works fine and resolves to proper mail or remote.contoso address. Problem is when I enter the RWA portal, of which I can do no problem with certificate mismatch which is pulling the mail.contoso.com certificate. When I try to launch remote connection to PC its giving me "Your computer can't connect to the remote computer because the Remote Desktop Gateway server address requested and the certificate subject name do not match. Contact system admin." If I go and change the certificate on the RD Gateway Manager to remote.contoso.com obviously this works fine. No mismatches and I can continue to go to Public/Downloads/Install Cert. Download and install on client and RDP works fine. Only problem is that the Exchange hosted on the same server with the mail.contoso.com will then give all the client Outlook users certificate errors as its pulling remote.contoso.com now instead of mail.contoso.com. SO..how can I get the TS Gateway to just use remote and the mail to use mail? Is there anything I could do with DNS but Im thinking it will still have a cert mismatch. This has been very frustrating to say the least and TIA for any assistance!
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Question by:iacovetti72
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Cris Hanna earned 2000 total points
ID: 37809397
SBS wizards are not designed to support multiple host names for SSL certs
OWA/Outlook Anywhere and RWA are in the same IIS site

The simple solution here is configure outlook anywhere to use remote.contoso.com

The other option is to re-run the Setup My Internet Address Wizard, select I have a domain name, select I want to manage it myself
When you get to the portion that says, enter Domain Name, click on the work "Advanced" under the text box
change Remote to mail, click ok, enter domain name and finish the wizard

Can you now connect to RWA and to the desktops with the https://mail.contoso.com/remote ?
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Author Closing Comment

by:iacovetti72
ID: 37813117
Since SBS 2011 has the limitation I went ahead and just used remote. and is working as normal. Thanks for your insight, as thats exactly what I was going to do but wanted to see if I could do something else.
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