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xpandit
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Logon Prompt Exchange 2007

Exchange 2007 runs on Windows Server 2008 x64. The same server is a DC. Environment has been stable for ages. I installed RPC feature and enabled Outlook Anywhere yesterday. The internal and external hosts are configured correctly and use the same name. Internal and External DNS just points to different IPs. I use a valid Thawte certificate.

Outlook now prompts for a password regularly. Both locally and remotely. Interesting it brings up th logon box with the servername in the username box and not the domain name. Any ideas why?

Exchnage Proxy Settings as follows:

The URL is correct.
Connect using SSL only is ticked. Only connect to proxy servers that have this principal name in their certificate is tciked.
The msstd: is correct.
On fast networks is unticked.
On slow networks is ticked.
NTLM authentication is ticked.
Windows Server 2008Exchange

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xpandit

8/22/2022 - Mon
Mestha

Sounds like autodiscover isn't working correctly.
I would be checking the URLs are correct to start with. While holding down CTRL, right click on the Outlook icon in the system tray and choose Test email auto configuration. Enter the email address and confirm that the URLs point where they should do and resolve correctly.

You can also test the site and its configuration using the Microsoft test site:
https://www.testexchangeconnectivity.com

-M
xpandit

ASKER
Great. Thanks.

Everything is correct. But if I compare this environment to my own, I see there are two entries missing under the section Exchange HTTP.
Availability Service URL is missing.
OOF URL is also missing.
Does that tell you anything?
xpandit

ASKER
I've added those URL's for the management shell. Its still prompting for username and password though. Have restrated IIS and reopened Outlook.
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rwheeler23
xpandit

ASKER
It is still prompting <SERVER NAME>\<USERNAME> rather <DOMAIN NAME>\<USERNAME>
Mestha

Are those URLs now being returned in the autodiscover test?
Did you restart any services on the server after changing them, did you restart Outlook?

The fact that you are getting a server authentication prompt is normal when Exchange is on a member server. It will attempt to authenticate locally.

-M
xpandit

ASKER
Exchnage is on a DC... The server itself is also a domain controller... Those URLs are now being returned in the autodiscover test. IIS has been restarted. Outlook has also been restarted.
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xpandit

ASKER
Thank you. Best Practices Analyser pointed out the OAB wasn't correctly defined for th information store. Or something like that. I corrected that and then restrted IIS and everything now seems fine.
Thanks again.