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Some users changed to a new email domain address; can't get auto replies or Out of Office to work right

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Hi, all! I hope I can get some help on this.

Same user, same server, new email address on new domain.

I have Exchange 2007 server, Outlook 2010 client. Some existing users need to change their email address to a new domain name, but they need to be able to access their old mailbox and leave an automatic reply on the old email informing of the new one.

So, John Doe has been using JohnDoe @ CompanyA .com. I would like for John Doe to login as usual, open Outlook and his email, which should now be JohnDoe @ CompanyB .com, send and receive using this new address and have access to JohnDoe @ CompanyA .com and an auto reply on it to inform the sender of the new address.

Almost all of this is possible simply by adding the new email address on John's Exchange mailbox and setting it as primary - John Doe can send from and receive to @companyB.com without a problem, emails are delivered to the same mailbox as before, etc, but I can't set an auto reply on one address and not on the other one. I've tried with rules "if a message comes delivered to this address, reply with this" but these rules don't work for some reason.

Then I started going down a different path - creating a new user and new mailbox for each person that needs to be in the Company B email domain, then have them leave an Out Of The Office in the CompanyA address informing of the new address, log in with the new profile, new user, new mailbox and add the old mailbox to outlook as secondary. All well and good, only that I can't have the OOtO reply go the same sender more than once. I want to have it responding always, no matter how many times the same person emails the old address. What happens if that sole time in which they receive the OOtO they don't see it? It wouldn't be the first time that somebody doesn't see an email. So auto replies don't work and OOtO are only sent once. Does it have to be SO HARD?? Even in Outlook 2003 I was able to set a rule "if I receive a message from This Person with This Text in the subject, send him an auto reply saying 'I keep receiving your emails' and delete it". I could in Outlook 2003 but not in 2010??

Please help. Thanks!


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