How to force Exchange 2007 to send to another mail system

I have multiple domains accepted on my exchange server. Recently, i've been asked to remove one and set them up in Google. My problem is once I do that and remove them from Exchange, my existing users will get failure notices because the accounts no longer exist in Exchange. Does anybody have any ideas how to get around this?
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ded2545Asked:
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ninjatekCommented:
The NK2 file (Outlook's cache) stores Exchange addresses in a different way to normal SMTP addresses (Use an app like NK2Edit to see the NK2 entries, Exchange addresses show as EX and normal SMTP addresses show as SMTP). If you think about it, if the old Outlook cached address was just a normal SMTP address then your Exchange server would route it to the correct destination as any other email address.

So when you add an address from the GAL it *should* pick it up as a 'new' address. You will have to test this out though. If for some reason it does turn out that Outlook keeps the old entry, the users will have to delete the cached entry first, and then add the address again. Depending on the size of your user-base, you could go round and use an app like NK2Edit to manually remove all the old entries, but that would be a very last move...

-Ninjatek
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Tony GiangrecoCommented:
You can add a forward on a mailbox to send mail to another address, but not forward all mail for every account to another system.

If you don't want the mail going into exchange, you need to hcange your MX records (or domain registration) so it points mail to the new mail server.
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John EastonDirectorCommented:
I use exchange 2003, but I expect the process is similar.

Once you have set up the domain with Google, you need to remove the domain from exchange recipient policies - and get this to update your users.  None of your users should then have an e-mail address for this domain.

You may also need to check your local DNS server to ensure any reference to this domain is deleted.  Also make sure that the external DNS is updated to point to google and not your server.  It could take a couple of days for the global DNS system to show the new details depending on server caching.

Hope this helps.
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ninjatekCommented:
Just to add to JEaston's advice:

Make sure you remove the Accepted Domain for the domain you are moving. Also, make sure your users don't use the cached email address, as this does cause issues - Get them to type it in manually for a little while, or create Exchange Contacts for the moved users and have them select from the GAL.

-Ninjatek
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ded2545Author Commented:
I'll elaborate a bit more ... i tried this on a single user domain as a test. I created the Google account and switched the MX records to point to google. External mail now flows to the Google servers and routes ok to the new mail box.

I removed the account in Exchange, removed the policy, and removed it as an accepted domain. When the user in the old exchange system tries to email the address, exchange spits out an error saying "that user does not exist"

Would this be an Outlook cache problem maybe?
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Neil RussellTechnical Development LeadCommented:
The problem that you almost certainly have is that of caching and replying to emails you already have.

When you send from outlook via exchange, outlook "Remembers" the actual exchange address of the recipient, NOT just their smtp address.

To get around this problem you will need to delete all locally cached contacts and all entries in the outlook quick lookup.

What you are getting is prob nothing to do with MX records.
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ninjatekCommented:
Yes, that is normally the case...If there are not too many email addresses being moved then you can create Exchange Contacts for them. This at least makes it easier for your users as they can select them from the GAL

-Ninjatek
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John EastonDirectorCommented:
Here is a link to delete the Outlook Address Cache.  Please note it will delete everything in the cache, and I have not tested the article.

http://www.howtogeek.com/howto/windows/outlook-2003/clear-the-auto-complete-email-address-cache-in-outlook/
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ded2545Author Commented:
I knew it wasn't an MX problem but i feared it was Outlook. By creating local contacts, how does that fix the problem when they are on another system?  I guess I was thinking there might be a way to force Exchange to send to google mail when a specific domain is sent to.

I don't know if your companies are like mine, but to some, it would be the end of the world if I deleted the outlook cache file!
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ninjatekCommented:
Haha, Yes, I know those users :-)

When I said create Exchange Contacts, I didn't mean in the Outlook Client. If you create Contact objects on the Exchange server, then they will be available to all your users (Outlook; OWA etc) through the Global Address List.

Let me know if you have any questions about this procedure...

-Ninjatek
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ded2545Author Commented:
No, i understood what you meant but correct me if i'm wrong .. all i'm doing by creating contact objects is assigning an email address to an object not stored on my exchange system. If someone were to email that object, would it not fail since the Outlook client is trying to access the old object?

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Neil RussellTechnical Development LeadCommented:
Yes you MUST remove the local references on the OUTLOOK clients. Just creating a new contact with the same SMTP address will not work.
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