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Outlook 2007 Password Prompt on second domain

Posted on 2013-10-24
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Last Modified: 2014-03-10
I have a couple of users setup on 2 separate sites.  One user account works correctly, everything appears to be setup identically. One user get a password prompt the other does not.

Setup is as follows Outlook 2007 and Exchange 2010, on both sites DC on site 1 is server 2008, DC on site2 is server 2012.

exchange1.domain1.com  Both users work at this site primarily and use this server for all email

exchange2.domain2.com  both users work here ocassionally, are domain users here and connect back to exchange1 for email via web proxy in outlook 2007.

The issue is when one of the users connects he is prompted for his logon for exchange1, which is normal then a few seconds later is prompted for a logon to exchange 2.

The user does not have an exchange account configured on Outlook for Exchange2 and does not need it.

The other user get the initial logon prompt for Exchange1 then goes right in as expected, but does not get the second prompt.
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Question by:ketol
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Will Szymkowski earned 1500 total points
ID: 39597358
What type of authentication are you using for Outlook? If you are using Basic Authentication switch it to NTLM. Also, if you create a new Outlook profile or start Outlook in Safe mode does it prompt a second time?

When the user encounters this are they actually connecting to the same DC/servers for Authentication? When you open Outlook right click on the Outlook icon in the system tray and select "Connection Status" verify both machines and see if they are authenticating to the same servers.
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