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Outlook is keeping old email account when email is migrated to Exchange

Good Evening;

Background: We are in the process of migrating from Zimbra (using the Outlook Connector) to an Exchange 2007 environment. We have found that the best way to move email to the new environment is prior to the user's migration, export all Outlook content as a .PST. When the system is re-imaged and Outlook 2007 is connected to the new Exchange server, the .PST is imported into the new environment.

Problem: When a user goes to reply to an email that was imported, the message will sit in their outbox indefinitely. Through further investigation, we found that Outlook tries to send the email using the old Zimbra server. If the user connects through OWA, this is not a problem and Exchange properly delivers the message.

Workaround: By installing a dummy 2nd email account into Outlook, the account button will appear under the Send button, allowing the user to select which account to send on. By choosing the Exchange account, the email will be properly delivered.

Now, my question is how force outlook to use the default email account for old messages and not try to send the email using an old, non-existent account. Is there a way to programmatically remove this metadata from the email headers? Can something be set in Outlook 07 to force this?

Thanks in advance
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ByramHC
Asked:
ByramHC
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8 Solutions
 
WilyGuyCommented:
Are you "importing" the PST as a separate mail folder or INTO the current structure?

What do the email accounts look like after the import?

Is outlook trying to use old server settings or just the old email address?
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ByramHCAuthor Commented:
I am importing the .PST (which was exported from Outlook, which was connected to the old Zimbra system) into the new system, new outlook, which is connected to the user's new exchange account.

On the new system, w/ new outlook, the only account is the new Exchange account.

Outlook is trying to send the mail using the old server/account, which is not present in the new outlook. The email addresses remain the same (the same address was on Zimbra is now present on Excahnge).
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WilyGuyCommented:
Can you try:
Go to Control Panel - Mail and remove all profiles
Recreate the Exchange Profile
Try to Re-Import the PST into the existing mailbox

In a worst case, you could "OPEN" the PST which is what makes it a new folder...then move the email from the Inbox to the Exchange Inbox and retry.  This won't help you for the Calendar/Contacts/etc, but will go a long way to determining the nature of the problem.

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ByramHCAuthor Commented:
Since this is a new system, the only profile on the system is the Excahge one. We have tried to remove the profile and re-download email - same problem. Whether we use cache mode or not, same problem. We've also tried opening the .PST and copying all email into the new profile - same issue.

Looking at emails affected byt this, you can see extra, old Zimbra inofmriton in the header:
X-Zimbra-Tags:
X-Zimbra-Flags: a
X-Zimbra-Received: 1208364982000
X-Zimbra-Modified: 1208365712000
X-Zimbra-Change: 11312
X-Zimbra-Revision: 11305
X-Zimbra-Conv: 3818
Received: from zimbra.byramhealthcare.com (zimbra02.byramhealthcare.com)
                by zimbra.byramhealthcare.com (Postfix) with ESMTP id A2BDC9C001
                for <xxxxxe@byramhealthcare.com>; Wed, 16 Apr 2008 12:56:22 -0400 (EDT)

I am looking to see if there is a way to remove this header information, either prior to the import or after the fact, as we belive this may fix the problem. We are currently playing with the scanpst utility to see if it can help the cause.
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WilyGuyCommented:
Here is a thought.... If the settings in outlook aren't changing AND the outgoing email is set right in the outgoing email and all that it is trying to do is "relay" through the wrong server, can you alias the name of that server (presumably it doesn't exist) to the IP of the Exchange server in DNS?
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ByramHCAuthor Commented:
I think the underlying problem is that Outlook is looking for an account on the system to send the email through, yet the account doesnt' exist. I will see if I can take a screenshot of what I am talkinga about.
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ByramHCAuthor Commented:
Here is an image...Notice in the notification bar that Outlook says "This message will be sent via Zimbra -", yet in the Account drop-down, Zimbra isn't an available account. The result is the message sitting in the outobx.
Problem.jpg
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WilyGuyCommented:
right, but what is the email address on the outgoing email? (check in the inbox and see what it is?)

Add the "From" to the message to see if it is populated.
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ByramHCAuthor Commented:
When I added the from box, the from field is blank. Also, when I reply to all, I am included in the reply list.
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WilyGuyCommented:
That is pretty consistent with normal outlook (the from being blank).

So if you SEND, and it goes to the outbox, can you open one and see the FROM address?
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ByramHCAuthor Commented:
In the outbox, From is still blank
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WilyGuyCommented:
Can you run a process monitor or sniffer to see what Outlook is trying to do with the email in the outbox?

Also, I assume newly created emails will go out normally through exchange?
And does that stop if there are other "bad" emails in the outbox?
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ByramHCAuthor Commented:
Newly created emails and new emails replied to go out without problems, regardless of whether or not a bad email is in the outbox. We will attempt to run a sniffer on it to see if we see anythihng
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ByramHCAuthor Commented:
It looks like it may have been the way we are importing the file. Zimbra saves it's data in a ".ZDB" file, which is basically a .PST. We've been renaming the file to .PST and importing that way. What we found is if we do a full export while still in Zimbra and take the new PST and migrate to the new system, we can then load it and run "scanpst", then the problem appears to be gone.

We will continue testing and let you know what we find.

Thanks for the help
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WilyGuyCommented:
Ah, very cool.  That'll be nice to have in the EE database.
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ByramHCAuthor Commented:
As previously stated, renaming the .ZDB to .PST and importing was the root problem. A full export and import solved the issue (w/ running scanpst).
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