Ex2003 Problem post Win2k8R2 install

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    We recently installed a Win 2k8R2 server into our Active Directory domain in order to ready the domain for Exchange 2010 servers to migrate to. We do not have the Ex2010 servers in place yet and have run into a problem that only appears to affect our VPN users.

    When the users try to log into Outlook they are greeted with an authentication failure. Due to network architecture we have three Windows 2003 servers still running and all of them, including the Ex2003 server have been patched with KB944043 in an effort to circumvent this problem. All affected machines have also had the patch installed with very random success. Despite all that the problem persists.

    There are no network connection issues between any of these machines and a domain controller at the time of the authentication failure. What’s most cryptic is that if the user waits roughly five minutes authentication will magically work and they’ll have access to Outlook/email for the remainder of the day.

    Has anyone ever run into this and can shed light on it? We probably won’t have Ex2010 up for another couple of weeks and will have to deal with this problem.

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