Background: I'm very used to Outlook 2016 with Microsoft Exchange functionality from my job and would like to use the same for personal email as well. My gmail address is my primary address, and I also have a .edu address that I use frequently. What I'm trying to achieve is:
- A single inbox for all my emails (gmail and edu addresses)
- Microsoft Exchange functionality (i.e., categories, flags/reminders)
- Ability to change the "from" address without it coming through with the "*** Email address is removed for privacy *** on behalf of..."
- Ability to use my gmail address as the default send from address
- For replies, automatically select the "send from" address based on the email address I received the message to
Steps so far: I initially tried setting up the gmail account as an IMAP account, but then the functionality is limited (i.e., no categories, flags, etc., which are important for my workflow). I now have my Outlook.com account connected to my gmail and edu accounts and am using my Outlook.com account in Outlook 2016 (as a Microsoft Exchange account). However, there are two drawbacks:
- I have to manually select the "from" email address for all outgoing messages because the outlook.com address is the default (i.e., I can't set the gmail to be the default, and I can't set it to base replies on which of my addresses the email was sent to)
- Even when I manually select the "from" address, it comes through as "*** Email address is removed for privacy *** on behalf of *** Email address is removed for privacy ***"
Any ideas? So far all I can think of is simultaneously using IMAP accounts for sending from the gmail and edu addresses (to avoid the "on behalf of"), but then I have sent emails in multiple places and still have to manually change the "from" address on every new email. I also tried setting the Gmail IMAP as the default account and then selecting "Always use the default account when composing messages" in settings, but that didn't work either.
