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Using Exchange 2007, a user mailbox has been setup with a primary email address set to "user@mydomain.com".

The user account is also a member of a distribution group where its primary email address set to "group@mydomain.com".

When an email is sent to the distribution group, the user receives the email and the distribution group name is displayed in the TO field.

In Outlook 2007, the default account is Exchange. An additional account has been setup with a reply-to address set to "group@mydomain.com". This allows the user to select between their own email address and the distribution group's email address at the click of a button.

When an email is sent to the distribution group and the user replies to that email, Outlook is always selecting the default account even though the email was actually sent to the email address of the "other" distribution group. Is there a way to tell Outlook to use the account for whichever the email was sent to in the first place? In other words when replying to an email, use the "default" account (user@mydomain.com) if the email was sent to "user@mydomain.com", otherwise use the "other" account (other@mydomain.com) if the email was sent to "other@mydomain.com".

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This is the behavior based on whatever account is the default. I don't have this issue in Outlook 2013. In my replies, my FROM changes to whomever the e-mail was originally sent to. There are likely some third party add-ons that can mimic this behavior in Outlook 2007. I recall having your same issue with Outlook 97, Outlook 2000 and Outlook 2003.

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