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Hi There, I'm not sure that you can do this automatically. When you reply to or forward a message it will go out via the same server that it came in on. When creating a new message outlook will use your primary email account. My default primary account has always been exchange and I have never had the need to change it. If you are creating a new message what criteria would you like outlook to use to choose an outing server assuming there was a mechanism available to do it?