Outlook: reply as email address the message was sent to

If I set up a mail forward so that [email protected] is directed to [email protected], and then monitor [email protected] in Outlook using IMAP, will Outlook (or can it be made to) reply to emails send to [email protected] as that email?

In other words can I maintain the illusion without the person I reply to randomly seeing references to my gmail account?

EDIT: I was doing some testing... When I sent from [email protected] AS [email protected], Outlook displays the incoming email as "[email protected] on behalf of [email protected]". I guess this means gmail's forwarding is not especially useful, is there a workaround? All my POP-based mail is rubbish compared to gmail...

Solution 1:

I came across this same conundrum. The problem on my end was I am using it for business as well and did not think the Gmail looked professional.

The way I had to set it up was to add the email as a POP account in Gmail - Settings->Accounts and Import. Even though I do not use POP to download the message, this gives you the option "Send through SMTP servers (recommended for professional domains)"

This will then use your SMTP servers and will hide any referring information from Gmail. Any mail sent via the Gmail SMTP servers needs to have the "on behalf of" information for spam tracking purposes.

Solution 2:

When you reply in outlook you can go to options and add the From field so you can spoof whatever email you want. In fact if you set that in the account properties so it always says you are someone else.

Anyway that is not a server related question...