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Exchange 2007 Autodiscover authentication issues...

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Last Modified: 2012-05-12
I had just finished migrating our user base to a new Exchange server running Exchange 2007 SP1 on a 2008 R2 server. All went well except that the users running Outlook 2007 or higher kept receiving certificate errors. After a bit of research, I employed the solution which was outlined in the article below:

http://www.shudnow.net/2007/08/10/outlook-2007-certificate-error/

While this did correct the certificate error, it caused all Outlook 2007 and above clients to continually receive a password prompt.

In our scenario, here's how it looks:

Server NetBIOS name: mail2
FQDN in Active DIrectory mail2.SOMEADDOMAIN
FQDN External: mail.somedomain.com

When I access the autodiscover service via mail2 or mail.SOMEADDOMAIN (https://mail2/Autodiscover/Autodiscover.xml), it prompts me for my credentials, which I provide and then it lets me through. However, if I access the service via https://mail.somedomain.com/Autodiscover/Autodiscover.xml, it will continually prompt me for my credentials and never let me through. I am not sure why this is happening, but I really need some help. I was not able to find this specific issue online which is why I am asking your assistance. Can someone please provide a solution?

Thank you all so much!
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Commented:
Hello,
The author of the article said :
You must also ensure there is a DNS record that allows mail.shudnow.net to resolve to your CAS
What the author of this article meant is that you need to have your internal DNS have a new forward zone called like your exernal domain and have in it an A record pointing to the CAS. Have you done it this way ?
Please double check your Autodiscover, EWS and OAB v'dirs > IIS> SSL settings > "Client certificate" should be ignored
Also check he authentifications on those v'dirs:
Get-AutodiscoverVirtualDirectory | fl *auth*
Get-WebServicesVirtualDirectory |fl *auth*
Get-OabVirtualDirectory |fl *auth*
Compare with > http://technet.microsoft.com/en-us/library/gg247612.aspx

Author

Commented:
Ha! Someone from Microsoft gave me the same thing. Thanks so much. I didn't quite understand all of the terminology.

Thanks!

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