Outlook: reply as email address the message was sent to

"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."

"The correct way to do this:

Go to tools > account settings > [select the account that you want to change the sending address of and click ""change...""]

In the ""Change E-mail Account"" popup you want to change the first email address field, and that will be the address that your e-mail recipients will see as the ""from:"" address.

Now if you don't change the SMTP server from Gmail to your original smtp server for the ""john@mycompany.com"" address your sent emails will say from: john123@gmail.com on behalf of john@mycompany.com. So change your smtp server to the correct one.

Note: You may need to go into ""More Settings"" > advanced > [and change the outgoing port/encryption].

Note also: If your new smtp server requires authentication, then again in the ""More Settings"" popup choose the ""Outgoing Server"" tab and select ""My outgoing (SMTP) sever requires authentication"" checkbox then select ""log on using"" option and enter the username and password for the ""john@mycompany.com"" account.

Your emails should now appear to be sent from ""john@mycompany.com"" even if ""john123@gmail.com"" is selected in the reply window."