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Hosted Exchange Prompting for credentials for old server

Posted on 2013-05-24
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Last Modified: 2013-07-25
Had Small Business Server 2003. Moving to Hosted Exchange. Autodiscover record points to Hosted Exchange. We are able to setup a new profile in Outlook for the hosted exchange mailbox.

When we open the new profile, we are prompted for the password for the hosted exchange mailbox. It accepts it and status of Outlook changes to 'Connected to Exchange'. After a minute or two, the status changes to 'Trying to connect to Microsoft Exchange' and we get another prompt for credentials. However, the credentials it is looking for are for the Small Business Server.

Also, it appears that we never get disconnected from Hosted Exchange because we can still send a receive mail. Just can't figure out why it is trying to make a connection to the old server.
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Question by:cnptechnologies
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by:Simon Butler (Sembee)
ID: 39196472
Have you removed Exchange from the old server?
Does the WINDOWS domain match your SMTP domain?

Simon.
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by:cnptechnologies
ID: 39196574
Exchange is still on the old server. The Windows domain does match the SMTP domain. Right now it only happens to two users. Not sure what is different about those two.
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by:cnptechnologies
ID: 39196632
If I take Outlook out of cached Exchange mode, everything works. I deleted the ost files and then put it back in cached exchange mode. When I open Outlook, it creates two ost files and is back to having the issue again.
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by:apache09
ID: 39198450
So why are two osts being created?

For some reason does the user PC have two different versions of outlook installed?

Is it possible there are multiple profiles setup on the machine?
Have you tried deleting and recreating the user profile

In the past have seen some similar issues where the previous exchange DNS was cached in outlook and it kept wanting to poing to the old one

We used Flush DNS to fix this

May also pay to check the versions on outlook being used
Make sure Office has the latest Service Packs installed

SHouldnt make a difference but would also check that any mobile devices that were sycing to the accoutns, had their Mail Accounts removed and recreated
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by:Simon Butler (Sembee)
ID: 39198906
I suspect it is Autodiscover that is causing this.
Autodiscover queries a number of host names - one of which is root of the SMTP domain:

https://example.com/autodiscover/autodiscover.xml

As you have the SMTP domain and the Windows domain the same, that means the root will resolve to the internal SBS server.

Did you create internal DNS records to match the external records that Microsoft told you to use? If not then you should.

However ultiamtely the problem may not go away completely until you remove Exchange and IIS from the old server.

Simon.
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by:cnptechnologies
ID: 39201618
Looks like if I uncheck 'Download Shared Folders' under Cached Exchange Mode settings in the profile, it doesn't prompt for passwords. Both users having the issue do not have any additional mailboxes configured in their profile. I don't know what "shared folder" it might be trying to download.

To answer the earlier responder, there is a CNAME record in the internal DNS that points to the Hosted Exchange for autodiscover. The profile has been deleted, along with the ost file, and profile recreated but still have the problem unless we uncheck 'Download Shared Folders' in the profile.

At this point, this are working so I guess I'll remove Exchange and IIS from the old server and see if that does it. Thanks.
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apache09 earned 500 total points
ID: 39202620
Have you tried to have a look in Send Receive Options?
Define Send and Receive Groups
Edit the Account

Possible you may see what Shared Folders its trying to download here.

Otherwise,
Id probably just clean the sharing on the users PC

You can do this by closing outlook and restarting using
Start>Run>Outlook.exe /cleansharing
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