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Logon to Sites message when opening outlook, SBS 2008

Posted on 2011-02-25
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Last Modified: 2013-12-01
I have a new SBS2008 installation with Exchange 2007 SP2 installed and my outlook clients are getting a login prompt every time they open Outlook that reads "Logon to Sites" or "Welcome to Sites".  You can can the prompt and proceed with no problems but this prompt is very annoying.  I believe I have the authentication set correctly in IIS.  Has anyone seen this problem?
Thanks
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Question by:ITLegal
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Expert Comment

by:markdmac
ID: 34987135
Make sure you have a public certificate, make sure it is configured in the SBS and also verify that the cert is selected in the TS Gateway Manager properties.
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Expert Comment

by:davorin
ID: 34992291
Check at outlook if you have set NTLM Authentication under Proxy authentication settings.
You can also try to set that on fast connections outlook uses first tcp/ip, then http
 Some more options:
http://www.petri.co.il/save-your-exchange-password-in-microsoft-outlook-2003-or-2007.htm
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Author Comment

by:ITLegal
ID: 35073978
I tried the NTLM setting, no luck.  The TM Gateway settings and remote web workplace certificate setup makes sense but I am not familiar with how to do it (if anyone would like to elaborate on actual steps).  I have a third party cert from godaddy that imported successfully but gave me an error that I need to import it into RWW.  The users are now getting a prompt to log into remote.domain.net.  The user names is auto populated at sites\username (not sure why it says "sites").

HELP

Thanks

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markdmac earned 250 total points
ID: 35079087
Go into the SBS console. Go to Network/Connectivity. Run the wizard to install a trusted cert and choose to use a cert that is already installed.

When that is done configure the TS Gateway, in Administrative tools, select TS Gateway Manager. There is a link ther to add servers to the farm. Run that and verify that your server is listed. There is a tab in there to select your certificate as well.
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Author Comment

by:ITLegal
ID: 35141501
I have done these steps and I am still getting a logon prompt for remote.domain.com when opening outlook.  I have covered every thing I can think of.  Any other ideas?
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LVL 27

Expert Comment

by:davorin
ID: 35154376
Here you have an article that could help you:
http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_2300-Outlook-continually-prompting-for-username-and-password.html

If you access OWA from that computer using your external name is the certificate trusted?
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