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troubled_iis_user

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Exchange Email Address Workaround

ok, we have a domain user that also has a hotmail account.  we wanted to combine them but did not want to use the internal address externally.  so this is how its working right now.  we have a pop3 connector that connects to hotmail and delivers all of the hotmail emails to the domain users exchange account.  then we set the default reply email address (in exchange) to be the hotmail address.  this way even when the user sends email from the exchange account it lies to the recieving server and says its from user@hotmail.com.  then if someone replys to that email it goes back to the hotmail account which is checked every 5 minutes by the pop3 connector and again delivered back to the users domain exchange account.  make sense? it works great (sorta).  here is the problem.  it works fine except when this user sends email to anybody @ hotmail.  these emails bounce back.  i'm guessing thats because it connects to hotmails server and says "this email is FROM user@hotmail.com" and hotmail is all like "well i know all of the servers that a hotmail email can come from, and your not one of them so you must be lying/spam." do you think that is what is probably happening? everyone else will accept mail from our exchange server telling the recieving server that the reply address is @hotmail.com.  anyway, if this is the case, does anybody know a way to get around this? we dont want to expose the domain email address, since this would confuse people with which relationships have already been built.  thank you in advance for any help you can provide.
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Muzafar Momin
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use hotmail pop account (configure it in outlook express) to deal to mail flow
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jar3817

What does the NDR say?

At first glance, I have a feeling since you set a domain account to have the email address of something@hotmail.com, exchange it going to think it's responsible for the hotmail.com domain. So when this guy sends to otherpeople@hotmail.com the server is trying to deliver it locally and bouncing because otherpeople isn't a valid local account.

If this is the case, or even if it is hotmail rejecting because you're forging headers, there really isn't much you can do about it. If this guy REALLY needs to use his hotmail email, I'd say just forward all his domain email to his hotmail address and setup outlook as a pop3/imap client for hotmail.
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very good jar3817, you are right indeed.  it is saying that there is no email address with that name in the system, but that isnt hotmail, thats my server!! i didnt realize that.  so since it is able to accept @hotmail email in order for the pop connector to work, it thinks it can deliver anything @hotmail locally.... any way to force this to always look externally?  even if that means it would do the same for all domains registered to exchange as valid.  we would rather use the exchange account than hotmail pop3 for obvious reasons. thank you
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jar3817

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i found a solution after you pointed me in the right direction.  i changed the "type" under Organization Configuration -> accepted domains... i changed the hotmail.com domain as type "External Relay Domain" it was set as "Authoritative Domain".  Thank you