Exchange 2010 Login Prompt

[pwaddington]

I recently upgraded exchange 2003 to 2010 and all mail flow (internally and external) is working fine. I have bought and installed a certificate and am able to connect smartphones to allow users to pick up their emails on their mobile devices.

The issue I am having is that users are being asked to re-enter their login credentials to outlook when its been open for 5-10 minutes. Strangely enough, the login prompt box gives the external address of our email server.

Does anyone on edugeek have a solution to this or have suffered a similar issue to this?

[tommej]

Hmmmmmm this rings a bell. Perhaps something to do with NTLM authentication and outlook anywhere.

This should fix it:

Exchange 2007 SP1 Outlook Anywhere NTLM authentication for domain based and workgroup based computers « Marc Kean

[sukh]

What is the cert assigned to and test email autoconfiguration and see what that comes back with.

[pwaddington]

The cert has 4 sans, the internal and external names of the exchange server, the auto discover name and the domain name.
The problem is with internal accounts connecting to exchange 2010 via outlook 2007. The username resolves fine and the user sees their emails fine. The problem occurs after about 5-10 minutes when the login prompt appears with the external name of exchange. If the user clicks off the logon prompt, they can continue working with their emails.

[sukh]

1. Can you insert a image of the prompt
2. What are you internal and external URL's for web services?
3. How many CAS servers do you have?
4. Did you do the test mentioned above?

[glennda]

try checking there isn't an old cached credential in control panel credential manager.