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I have emails for two addresses coming into my inbox (emails to both addresses show as coming to my name).

I would like to have two different Automatic Replies sent - one for emails sent to me and one for emails that were actually sent to the other address (that of my boss).

Outlook 2010 only seems to have the capability to set one Automatic Reply, so I set this with the reply I wanted to go to my boss' emails. I then set a rule saying that emails sent to my specific email address should have a different reply, using a template I set up.

The rule doesn't seem to be kicking in, however. Can anyone shed any light?

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All Email Accounts will Auto Reply from outlooks default sent folder. You need to Change sent setting from each email to send from the email account it self instead of the default sent folder. Then you can save 2 auto replies for each email account. Just make two different templates and save them with obvious names. Then Apply that rule to that email account.

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The automatic reply feature is really just a shortcut for making a special rule (it does not show in rules though). Setup your automatic reply as you always do for one address, and for the other create a rule. You create the rule by going to the Home tab>Rules>Create rule. If you highlight the e-mail you want to base it on, it will attempt to guess as some of the things you have to fill in.

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