I've been using Google Apps for years. Now I am thinking about switching to Outlook.com/Office 365. Note: I am not and won't be using Outlook for Windows.

The one feature I find invaluable with GMail is "Reply from the same address the message was sent to". The only thing I do to set this up is in Settings->Accounts I need to add an alias email. Easy enough.

I don't have to do anything else. When I reply, the From: address is automatically set to the address the email was sent to. Great!

Does Microsoft in Office 365 (I'm not interested in Outlook for Windows, I wouldn't use that) offer the same feature without having to go through a complicated setup or hack?

Thank you.


Unfortunately Outlook for Web Access will just reply using your default e-mail address. I added my gmail account and they loaded into the inbox.

In Outlook for Web Access, the from ended up being my work e-mail.

If I use Outlook for Windows (newer versions anyway, such as 2013/2016 and maybe 2007/2010) it pretends to have the correct FROM e-mail, but unless you've actually added that account to Outlook (Windows), it'll just use the default e-mail address.

Outlook for Web Access (OWA) is a competent web mail client, but the features diverge quite a bit from Gmail.

Personally, I think you'll be disappointed with any type of switch from Google Apps as it relates to replying back with the correct FROM.

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  • To Add to @LunaMezza it's pretty difficult to setup. In Outlook to use an Alias we needed to connect a 2nd account thru POP, and disable the email checking, this allowed it be selected as an address. Other options are creating the alias on a distribution group or shared folder and granting yoru self "send as" permissions. None of these is ideal. – Jesus Shelby May 4 '16 at 20:43
  • @LunaMezza thanks for your input. I'm sticking with Gmail then. No alternative. – John May 5 '16 at 7:57

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