Outlook Anywhere almost working fine

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Tim Chapman

I am publishing an Exchange 2010 CAS behind ISA 2006 SP1. The same public UC certificate is on the CAS server and the ISA server with the subject name mail.domain.com and a SAN of autodiscover.domain.com.

Outlook Anywhere is using NTLM authentication.

External Outlook Clients connect almost immediately, (status bar says 'Connected'). A few seconds after connecting a credentials prompt pops up saying 'connecting to autodiscover.domain.com'. On entering credentials that is the end of it, all is fine.

I am trying to prevent that credentials pop up occuring, after all Outlook is already connected and new email appears. As far as I can see all the Exchange Virtual Directories have been set to use Basic and Windows Authentication.

Any clues about why the autodiscover url is prompting for credentials after Outlook is connected?

Should also mention that ISA is not authenticating the user but passing authentication straight throught to the CAS

Ed Crowley [MVP]

If the clients are using Outlook 2007 or higher, then they use Exchange Web Services and the Availability service for free-busy, the offline address book, and other features, so they must make a web connection. Perhaps that is what's causing your delay. You can use Outlook's "Test E-mail Connectivity" feature to see what URLs are being published so you can trace the authentication mechanisms.

Is there any particular reason you're not having ISA do the authentication?

Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Novak Wu

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