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I'd like to know if it's possible to configure Exchange 2010 to read x-headers from an outbound message (say, user@internaldomain.com to user@yahoo.com) and then re-direct the message to an alternate smarthost if the x-header is present. Does anyone know if this can be done?

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in exchange 2003 if I recall this was possible by scripting an outbound filter and applying it via the admin console, I used to have this occur to apply legal disclaimers for all outbound mail. I can't say for sure with EX2010 as I do not have a deploy to experiment upon. – Oneiroi Mar 20 '12 at 14:31
Cool info. Thanks @Oneiroi – Mike B Mar 20 '12 at 18:33

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This can not be done out of the box. However it can be done with several third party extensions or you can write a custom transport agent if you have .net experience.

Sample Code::How to control routing from your own routing agent

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No - at least not as you're describing it.

In ESM, look at your Organization Configuration | Hub Transport | Transport Rules. One of the Conditions you can configure is when the message header contains specific words. If you look at the Actions step of the wizard, you can fiddle with the message itself - adding recipients or putting a legal disclaimer in the body. What isn't there is anything that can directly change the message's routing.

There are third-party products that will choose a smarthost based on sender - but a quick search doesn't seem to turn up anything that works on a message header.

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