Repeated Password authentication requests from Outlook Anywhere on a Server 2008 Exch2007 domain

Posted on 2009-04-29
Last Modified: 2012-05-06
HI All

We are having trouble with Outlook Anywhere and our new 2008 domain. We have the following setup:

DC = Windows Server 2008 SP1
Exchange Server, OS = 2008 SP1, Exchange Server 2007 SP1

The Exchange Server contains all exchange roles (apart from edge). We have mixed 2003 and 2007 Outlook clients.

We started having trouble with Outlook 2007 clients internally being asked for a password repeatedly  which when entered wouldn't connect so we cancelled the box and used the TYPE password and connect option and that connected outlook temporarily.

After reading another EE arcticle we tried disabling Autodiscover's basic authentication in IIS7.0 and restarting the IIS admin service.

This seemed to fix internal clients but then Outlook Anywhere got repeated requests!!

We rolled back to basic authentication on autodiscover to try to prove a point and so far internal are still working? However Outlook Anywhere (after and initial success) is still not connecting and still exibits the repeated login boxes with no connection.

It's very strange..

We have found stuff out on the web about a bug with IPv6 but would like to post here to see if anyone can corroborate that theory.
Question by:StevenMooreSmartsoft
    LVL 6

    Expert Comment

    Do we have the latest rollup installed on Exchange 2007? If the rollup was not installed successfully, then it can cause such issue. In that case, uninstall & reinstall the rollup.

    Author Comment

    Yes Security rollup 7 is installed on the Exchange Server but it was working ok after that, but we will keep it in mind and there is no indication it didn't install properly as Outlook Web Access is working and that normally screws up when the rollup fix.


    Accepted Solution


    A Microsoft Support call fixed the issue. It is a known issue with them and I got the support cost refunded...

    Turn off Kernal mode authetication from IIS 7, Advanced settings of Windows Authentication for Autodiscover, EWS, OAB and RPC virtual directories. Then do an iisreset cmd from the command line to restart IIS.

    Our internal OAB address also had to be changed from http to https as we where using Outlook Anywhere.

    In Exchange System Manager. Server Config > client access > Offline address book distribution tab > properties of the OAB

    This seems to have fixed both the internal side and the Outlook anywhere side. I will need to wait 24 hrs before I'm convinced by it's looking good....

    Good luck..

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