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[MS Exchange 2010] Auto-reply all external incoming messages

We are going through a branding process the next month. Goal is to change the domain name for our company email addresses asap. Marketing requested us to setup an auto-reply with our new email addresses for all incoming messages pointed to our old email addresses for a period of two months. During this period all messages still need to be delivered.

After this period of two months we need to send an auto-reply that the email address is no longer valid and messages need to bounce. This way we want to force external contacts to start using our new name and email addresses.

Ideally would be to mention the new email address in the auto-reply (using %username%@xxx.com perhaps?)

Can above steps be performed withing Exchange 2010 or do I need a third party tool?

If I need an external tool, what tool would be best to use? Also if we need to purchase software it would be ideally if it could also manage signatures from the Exchange server so all employees don't have to update their signatures individually every time it changes.
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MatthiasSmit
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MatthiasSmit
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tigermattCommented:

There is no built in support for this in Exchange 2010 - you would need to use a transport rule, but there is no action to send an auto reply. This is for a good reason: without careful monitoring and tracking of auto replies, you can end up in a message loop which will eventually cause issues for either you or a sender's server.

I do believe Exclaimer has support for this though: http://www.exclaimer.com/products/AutoResponder/Default.aspx, whether it will do exactly what you ask for is something I would recommend you test yourself in their trial version.

As far as changing the email branding goes, I can fully understand and appreciate re-branding a company. However, marketing will sometimes come up with... interesting... ideas without any appreciation for the technical aspect of their plans.

Simply blocking emails to the old domain is not practical and certainly doesn't represent a professional image if a sender has to re-send their message to a new domain. It will result in lost business, which means lost money. There are also the issues of auto-mailers configured with the old names which users won't be able to track and change until it may be too late.

My preferred change would be to phase in the new email addresses so that users send and receive on the new address but keep the old address. Given time the older addresses will naturally fall out of use.

-Matt
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MatthiasSmitAuthor Commented:
Thanks for your quick response! I will try Exclaimer, once I know this meets the requirements I will mark your answer as Accepted.

On the branding part I completely agree with you and have had this discussion multiple times but I haven't been able to change their mind. Management seems to agree with Marketing but with above arguments I will start another discussion, thanks for thinking with me!
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tigermattCommented:

Absolutely no problem.

When you have to drop all email entirely, I did consider a possible Exchange transport rule action which can help you. It's called "Send bounce message to sender with enhanced status code" and can be found in the usual transport rule location (Exchange Management Console > Org Configuration > Hub Transport > Transport Rules).

However, that isn't helpful during your co-existence period because it will literally bounce those messages with a non-delivery message to the sender.

The other issue to remember with auto responders if you are taking it up with management is you might end up responding to spam... which isn't something you really want to get into. It could wind up getting you blacklisted, especially if the spam has spoofed sender headers -- someone would be unwittingly bombarded with bounce messages which they report as spam, or abuse to your ISP, and you will get cut off. That isn't fun at all.

Unfortunately, the non-technical departments don't always respect the technical difficulties of a particular request. I believe that's a problem we are all destined to experience at one point or another.

Best of luck!

-Matt
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Neil RussellTechnical Development LeadCommented:
The only safe way to do this is to put an Autoreply rule on to every users account via outlook.  That will avoid the Issue of emails sent to non existant accounts getting replies as well.
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tigermattCommented:

Strictly, I was referring to spam sent to users who do exist. No auto responder is ever going to be able to pick out the good from the bad, which is why I don't like them, full stop.

Messages sent to users who do not exist will be picked up by anti-spam filtering on the Edge Server (or the Hub Transport if no Edge Transport). This should be doing Recipient Validation to ensure valid recipients are specified in the SMTP session RCPT TO command, and if invalid entries are provided, it terminates the connection rather than proceeding.

This won't lead to an auto-responder replying because the message hasn't been accepted by Exchange when the SMTP session is rejected. As a result, it isn't in the appropriate part of the transport pipeline at that stage.

-Matt
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MatthiasSmitAuthor Commented:
I have received enough valuable information to submit the points. We are going to start another discussion with Management/Marketing using the giving arguments. Thanks!
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MatthiasSmitAuthor Commented:
Just to inform you, with help of the arguments mentioned above we went into another discussion with management and marketing. This time we involved our CEO who agreed with us and he convinced everyone that the auto-reply was a bad idea. Thanks!
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tigermattCommented:

Excellent news! Well done! I'm pleased to have been of assistance.
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