Outlook asking users to login to exchange and security certificate

We have a mixture of exchange 2003 and 2007 server. Our goal is to eventually only have 1 server running the Hub/CAS another one running just the mailbox while the final one would be running the edge. So far we have done that, however we want to decommission the 2003 server which use to run the whole environment and also one that was initially running exchange 2007 and all the roles. So far the decommission is running but we have came across number of problems.

1. Outlook is now asking users to provide username/password for the 2003 server which is incidentally not running any roles what so ever now, the login dialog box appears every time they start their outlook. What could possibly be causing this and how can we stop this.

2. Outlook 2007 is displaying the security Alert about the server certificate, my question is is there a way we can stop this security alert popping up without buying a security certificate from one of the known companies?

Thanks in advance for your help.
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1. What did you do with Active Directory? There are no exchange passwords only Ad passwords so how can the system as for Exchange 2003 passwords.

2. If your computers are on a domain and accessed internally only you could deploy your own certificates.

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aniga42Author Commented:
We did not do anything specific to the AD. Our RID (Relative Identifier) master was down as the old server that had that role gave up on us so the only thing we did was seize it from that server and assign it to one of our other servers.

If we deployed our own certificate wouldn’t it still say this certificate is not from a known issuer?
What makes you think these passwords are for the old 2003 server then?

You can use Group Policy to force machines that are in your ad to trust your certificate. From looking at this:-


it appears if you deply an enterprise root it will automatically be trusted by all computers that are members of the domain.

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aniga42Author Commented:
Thanks for the response,

The dialog box asks us to connect to the this particular server as per the attached image, thus we are sure it is the 2003 server (which incidently is also one of our AD).

I will read through the technet article you posted and report back.

Any other ideas about this dialog box?
If the server was also a DC did you "un-promo" it before you switched it off?

If you go into Exchange System manager and look at your new Exchange Server Properties, Directory Access Tab, does it still show the old DC?
aniga42Author Commented:
Fixed it while using some ideas from the expert but olso combining it with our own internal team
RhiannonDeThomasSystem EngineerCommented:
aniga42:  I am running into this exact issue.  Only on our Exchange Server at our remote site.  What was the fix?????
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