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tigermattFlag for United Kingdom of Great Britain and Northern Ireland

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Autodiscover connecting to internal AD

A quick one for you guys, but I'm going around in circles trying to find a fix.

I've taken on a job to troubleshoot an Exchange 2007 Server on a Server 2008 Standard Edition machine. A SAN certificate has been installed, which has the domains mail.company.com, servername, servername.ad.company.com and autodiscover.company.com listed. (mail.company.com being the Common Name, the others being Subject Alternate Names).

The firewall has already been configured to allow port 443 through to the server, URLs updated in Exchange and the SSL certificate installed. Outlook (on a non-domain joined machine) does seem to work. However, it is painfully slow in the initial discovery and start-up phases.

What seems to be happening is Outlook is attempting to connect to the internal server name (servername.ad.company.com) rather than the external name (mail.company.com). I've checked every location in Exchange but cannot find where the wrong URL is located.

Any insight would be appreciated as I'm going round in circles. Thanks.
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kevala

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Well, I've advanced a lot in the last 12 hours. This server had been completely incorrectly configured, which was the cause for Autodiscover to be very slow.

In short, this is what I've now done:

Re-keyed the SSL certificate with the supplier and re-applied the SSL certificate
Reset the configuration of the various Exchange Virtual Directories
Fixed the EAPs and Accepted Domains lists, to include only the client's main domains and none of the other rubbish which was in there
Disabled Autodiscover, rebooted, re-enabled.

And it is now much, much quicker - in fact, whereas configuration in Outlook could take upwards of 5 minutes to detect and make the initial connection, I just made a connection in less than 15 seconds. So, a lot quicker!

Thanks for your help guys. Simon, that test site is particularly useful and is now in my bookmarks. Thanks!

-Matt
All useful information, thank you!