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We have a shared exchange mailbox with multiple SMTP addresses;,, and so on.

When a user replies to a mail in this mailbox we want the from: field to default to the address the original mail was sent to; so if a mail was sent to the reply should come from and not the default

Users can change the from: address manually per email, but that is leading to mistakes as they leave it on the default value.

Is there any way to change the default from behaviour in this way?

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up vote 2 down vote accepted

Separate mailboxes are the way forward I'm afraid, there's no native functionality in Outlook to allow the picking of a secondary SMTP address over the primary or another secondary.

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Well, there is the one way, natively. Seems that OP's users keep mis-clicking when using that native function, however. – HopelessN00b Sep 26 '12 at 7:04
Hopeless N00b is exactly right, that why I want to automate it if possible. – DrStalker Sep 27 '12 at 3:43 has a pretty comprehensive list of possible workarounds.

Essentially on the server side (does not work for hosted Exchange of course), you can use AD contact or a Distribution Group. There are also some third party solutions (such as ChooseFrom and SmartReply from IvaSoft).

On the client side (works with both on-prem and hosted Exchange), you can add a POP3/SMTP account in Outlook for each alias, but you need to make sure POP3 does not retrieve and/or delete the messages.

You can also try Proxy Manager - it sends through SMTP, but to an end user it looks like the message is sent by Outlook, and the experience is the same as having a POP3/SMTP account for each proxy address (the user selects the address from the From drop down and clicks Send).

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