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For example, if I have a mailbox joe@work.com which is a member of the list joe@shmoe.com which goes to a matching folder in the Work.com mailbox... When Joe replies to a Shmoe email, I want the from address to fill with Joe@shmoe.com

Specifically focused on Outlook 2010 or Outlook 2013 connected to an exchange mailbox. Third party add-ons are ok so long as they are reliable, don't cost more than $100, and are client side only (don't want to install more software on the exchange server)

Why: We are a managed services firm who do work on behalf of several companies so we often need to send from different addresses. Since exchange insists on overwriting mailbox aliases with the default both in received email and sending email, we've had to set up different distribution groups for each alias we want to send from. We then enable the From box in outlook and have them manually enter whatever "alias"(distribution group) they want to send from.

This works fine for most users, but the CEO doesn't like having to manually enter a From address every time they're replying on behalf of one company or another, they want the from address to always match the account the emails were sent to. This isn't just for convenience, it's to make sure they're always using a matching address when sending to outside contacts.

Initially we tried setting up separate mailboxes for each of this users aliases but this isn't working out for them, so I had the idea of possibly setting up mailbox rules to funnel the different lists into different folders. I'm hoping there's some way to have the from address auto fill based on the folder (or some other criteria, I'm open to alternate suggestions)

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Pretty sure what you want to do isn't possible.

The additional mailbox method is the usual route for this, as Outlook will automatically fill it in based on the mailbox selected when replying.

The only third party tool that does anything with email address selection is ChooseFrom from ivasoft.biz. However I am not sure if that can do the automatic selection that you desire.

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