Outlook: reply as email address the message was sent to

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If I set up a mail forward so that john@mycompany.com is directed to john123@gmail.com, and then monitor john123@gmail.com in Outlook using IMAP, will Outlook (or can it be made to) reply to emails send to john@mycompany.com 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 john123@gmail.com AS john@mycompany.com, Outlook displays the incoming email as "john123@gmail.com on behalf of john@mycompany.com". 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…

Best Answer

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.

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Change the “Reply to:” options on iPhone

With ActiveSync (i.e. Exchange type account) Here's how to work around this problem;

Go to Settings > Mail, Contacts, Calendars > [Your Google Sync Account] > Account Info and change the Address field to the email alias you normally send from (this will be use as the default when ever you want to answer emails)
Create other email accounts by following these instructions with one exception. On step 7 enter the email alias instead of your GMail address for both the address field. You may want to use good description for this "bogus" account.
Once you have done the final save, tap on the account you've just created and erase the Incoming Mail Server Host (imap.gmail.com). It's important to leave this field blank since it will prevent you from receiving duplicate email. It will however still allow you to send outgoing from the email account you've just created

To select the source email address when you reply simply tap on the from field and a rolodex will let you select your from address.

They are two caveats to this however

The iPhone mail application will not select the from address automatically. It will always default to the email address you've set at step 1 even if you are replying to an email sent to one of the aliases.
Since this involve creating a "bogus" account in the iPhone mail application every time you'll hit the refresh button you'll get an error message stating that the iPhone cannot retrieve email from the dummy account. The error repeats itself for every "bogus" account.

Some other people may like to know that for any IMAP account in the iPhone Mail application you can always go into Settings > Mail, Contacts, Calendars > [Your IMAP Account] and change the Address field to a comma separated list of email address that are associated with that account. Since the field will not let you put in a comma directly you'll need to use paste the list in the field. The list itself should look something like this:

myFirstAlias@company.com, mySecondAlias@company.com, myThirdAlias@anotherdomain.com

Outlook – Extract reply addresses from all emails in an outlook folder (sent on behalf of)

In the end, I found what I needed using the free CodeTwo Outlook Export utility

It's fairly straight forward, but I've written full instructions on my blog.

Best Answer

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Change the “Reply to:” options on iPhone

Outlook – Extract reply addresses from all emails in an outlook folder (sent on behalf of)

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