As a GMail user, I much appreciate that when I "reply" to an email sent from me, it knows I want it to replicate the To: field, not move the From: field to the To: field. Outlook does this if I "Reply All" to an email entry in my "Sent Items" folder, but if I just "Reply", it addresses the message to me. Is there a way I can tell Outlook to behave like GMail?

  • Thunderbird is also clever enough. Outlook 2016 is still "stupid". – Jack Miller Aug 17 '17 at 6:31

Unfortunately, no. You have to use the "Reply All" button on sent items.

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