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Strange outlook 2007 / Exchange 2007 problem – password prompt

Posted on 2010-11-13
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Last Modified: 2012-05-10
Folks

I’m having a strange problem with a Win 7 / Outlook 2007 machine.

We have recently installed a new SBS 2008 server on this fairly typical & plain vanilla small office network (they did not have Exchange up to now).

Everything went smoothly with most machines (a mix of XP / Vista / Win / running Outlook 2003) except for one single workstation which is running Win 7 and Outlook 2007.

On that machine whenever launching Outlook the initial config works fine (i.e. the server is auto detected) but as soon as Outlook is loaded the user is prompted of a password. The interesting thing is that the password is apparently sought for a machine named “remote.mydomain.com” which is the external DNS name for the site (the public IP being configured on the SBS server in the various wizards) and not for the internal Exchange server name. No matter what is entered the prompt is recurring every few seconds but interestingly enough the mailbox is still updated from the server, even if the password dialog is dismissed.

I have tried

to re-create the mail profile from scratch
to reinstall Office 2007 with latest patches
to edit the host file in order to forward remote.mydomain.com to the internal Ip of the exchange server
to connect using HTTP/RPC
to use the various authentication methods
to remove all anti virus
to edit the registry as per KB 956531
to access the mailbox through OWA, which works perfectly

as this stage I am pretty much stumped…

As such any idea / suggestion most welcome
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Question by:atak2983
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5 Comments
 
LVL 9

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by:ken2421
ID: 34129232
@atak2983

I have found that http://www.microsoft.com/downloads/en/details.aspx?familyid=6a894b4e-12b6-4a91-9555-d813956b6aac&displaylang=en
is a very common problem with a good solution.

HTH,
Ken
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Accepted Solution

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tstritof earned 500 total points
ID: 34129349
Hi,

I've usually had this problem in several situations:
- when connecting non-domain connected clients to Exchange,
- when running some specific VPN clients with Outlook already opened.

In first situation it was a matter of trusting the Exchange server. In the second situation it was caused change in domain suffix after starting VPN client.

So I'm guessing that the symptom you are experiencing might be caused by remote.mydomain.com certificate not being trusted by your client or certificate served by Exchange not containing that external name.

If that's true then you should be OK after you fix certificate issue.

However, there may also be something wrong with your DNS/DHCP setup to begin with since your SBS fqdn resolves to public name. But since this doesn't happen on other computers maybe you should check your NIC IP settings on affected computer first. BTW, if your internal domain suffix is the same as your public domain please ignore this paragraph.

Regards,
Tomislav
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Expert Comment

by:endital1097
ID: 34129445
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by:ahdfx
ID: 34129855
in Outlook, Go into the Account Settings-> Properties. Check in the more settings button then to security.
Is the Check box checked for "Always prompt for logon credentials"?

What is the Logon network Security set to?

Under the connection tab, are you using Exchange over Http?
If the computer in the same network, turn it off,
If on a different network, check the settings.
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Author Closing Comment

by:atak2983
ID: 34132346
Turns out that it was indeed some sort of certificate issue. I have logged from the problematic machine to OWA and installed the self signed cert to the machine's repository. All is well (although I'm not 100% sure *why*).
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