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Microsoft Outlook 2013 security screen on Exchange 2007

Posted on 2014-02-02
Medium Priority
Last Modified: 2014-03-15
We have upgraded our MS Office to the 2013 version and we having a lot of problems with Outlook, it is connected to our SBS Windows 2008 with Exchange 2007 and it keeps asking for credentials, once Outlook is open, not only when you open it  but also while it stays open. It says Windows Security, Connecting to user@abc.com username/password, the strange thing is that our domain is .local but on the connection screen tries to connect to our web domain .com

Any help will be appreciated.
Question by:jdff
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LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 39828867
The references to your public domain are the expected behaviour.
SBS 2008 and higher will configure Exchange to use remote.example.com for web services, which includes things like Autodiscover, rather than your internal host name.

Do you have a trusted SSL certificate on your server?
If not that is the primary reason for the authentication prompts. The recent versions of Outlook are lot picker about SSL certificate trust issues and you should be using a trusted certificate.


Expert Comment

ID: 39828918
Hello, we in our organization was the same problem.
this problem can be for 2 causes :
1-TMG (we did a re-installation of this server)
2-you can change in the outlook 2013 the "Microsoft exchange proxy configuration" (image attached)

Good luck!

Author Comment

ID: 39829461
We don't have a proxy server here.
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Author Comment

ID: 39831414
Simon, yes we do have a SSL from enom installed in the server, should I tell outlook to use it? and if yes, where do I put the settings?
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 39832129
If you have a trusted SSL certificate, was it installed with the SBS SSL certificate wizard? If not then you need to go back and correct that.
You don't do anything on Outlook, that isn't the way things are designed to work. It is all server configuration, and with SBS that means running the wizards.


Author Comment

ID: 39834505
Yes, the SSl was installed with the wizard, so what should I do now?
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 39838361
Does the host name on the SSL certificate resolve to the Exchange server's internal IP address? When you get the SSL prompt, if you look at the SSL certificate, it is the expected certificate?


Accepted Solution

jdff earned 0 total points
ID: 39841146
This fixed.

On the workstation to the following.

1. Click Start, and then click Run.
2. In the Run dialog box, type regedit, and then click OK.
3. In Registry Editor, go to the following registry key:
For Outlook 2010:
4. Add the following Autodiscover entries:

Author Closing Comment

ID: 39931065
It's all fixed now.

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