Reply to email from forwarded email account using original email address with Gmail as forwarding target

Question

This is pretty much the same as Reply to email from forwarded email account using original email address except, apparently, that I'm using Gmail as the forwarding target. I've done the settings suggested by https://superuser.com/a/733268/423386. Neither worked for me.

I'm using Outlook for MS Office 365. For a personal email account I use a forwarder so my address is [email protected]. This is forwarded to a Gmail account, [email protected], that has IMAP/SMTP access enabled. I'd like people I correspond with to only use the forwarder address since the account it's fowarding to can change. So when I send an email, it should show the sender as [email protected].

I've set up the Outlook account for the [email protected], with "Your name" set to "me" and "Email address" set to "[email protected]". However, when I send an email, the sender is shown as "[email protected]". How can I fix this?

I'm not trying to fool anyone here. Someone who cares can easily find out the Gmail address. What I want is that a recipient can just click Reply and the reply will be sent to the forwarder address, not the Gmail address.

I've done this very thing successfully when forwarding to an email account, [email protected], on a hosting service and it works fine. But it doesn't work for Gmail. Is there something special about Gmail that's causing this? Or am I missing something?

Answer 1

The devil's in the details between the various problems and solutions you referred to however what follows is a solution targeted specifically to your requirements.

Assumptions

1. You have an email address [email protected] that you forward to your personal Gmail address [email protected]

2. You want to send and receive email for [email protected] in both Gmail and Outlook.

3. You are not trying to trick anyone^* however you want sent messages to have [email protected] as the 'From' address not [email protected].

   ^{* Message headers will expose your Gmail account}

Instructions

Complete the following steps:

1. Gmail: Add 'Send mail as' address
2. Gmail: Configure 'Send mail as' settings
3. Gmail: Ensure IMAP is enabled
4. Outlook: Add Gmail account
5. Outlook: Modify 'Send/Receive' settings
6. [Optional] Outlook: Override 'Send Mail as' when desired

Step 1. Gmail: Add 'Send mail as' address

1. Navigate to the 'Send Mail as' section in Gmail Settings > Accounts and Import
2. Click 'Add another email address'
   
3. Enter the 'Name' you want displayed on sent messages, the 'Send mail as' address, then click 'Next step'.  For example:

            Name: blearyeye
   Email address: [email protected]

   
4. Click 'Add account' after populating the SMTP server settings using your forwarder.com account's info (not Gmail's).**  For example:

   SMTP Server: smtp.forwarder.com  Port: 587  
      Username: [email protected]
      Password: <[email protected]_password>
      ☑ (checked): Secured connection using TLS (recommendeded)

   
5. Close the confirmation dialog window, then click the link in the verification email sent to [email protected] and on the approval page click 'Confirm'
   <sub>Confirmation Dialog
   
   Verification Email
   
   Approval Page</sub>
   
6. Once the 'Send mail as' address is successfully verified, proceed to Gamil Step 2

Step 2. Gmail: Configure 'Send mail as' settings

1. Navigate once more to the 'Send Mail as' section in Gmail Settings > Accounts and Import
2. Make [email protected] the default 'Send mail as' address by clicking the 'Make default' link to its right.
3. Enable the option 'Always reply from default address' if not already set.
4. Following these steps the 'Send mail as' section should now look like:
   

Step 3. Gmail: Ensure IMAP is enabled

1. Navigate to the 'IMAP access' section in Gmail Settings > Forwarding and POP/IMAP
2. Enable the option 'Enable IMAP' if disabled and configure any additional IMAP settings as preferred. Note that unlike Gmail settings that are automatically saved when changed, changes to this section require you to explicitly click the Save changes button.
   

Step 4. Outlook: Add Gmail account

1. Open Outlook and click the 'Add Account' button under File > Info (Account Information) > Add Account
   
2. Type in your Gmail address [email protected] then click 'Connect'
   
3. Complete the 'Sign in with Google' process.
   
4. Click 'Allow' in the verification window titled 'Microsoft apps & services wants to access your Google Account'
   
5. Exit the 'Add Account' dialog

Step 5. Outlook: Modify Send/Receive settings

1. Access the 'Define Send/Receive Groups' settings using Ctrl+Alt+S or from the ribbon menu Send/Receive > Send/Receive Groups > Define Send/Receive Groups
   
2. In the 'Send/Receive Groups' dialog click 'Edit'
   
3. In the 'Send/Receive Settings' dialog make sure that your Gmail account [email protected] is selected, and click 'Account Properties'
   
4. In the 'Internet Email Settings' dialog:
   1. [Optional] Change the 'Mail Account' name on the 'General' tab from [email protected] to [email protected] or something else. This change has no effect on the account settings themselves and only affects the way the account is named in Outlook lists and menus.
      
   2. On the 'IMPAP Email' tab change the Email Address in the 'User Information' section to [email protected] then click 'OK'.
      _{^{Do NOT change anything in 'Server Information' or 'Logon Information'}}
      
5. Click 'OK' to exit the 'Send/Receive Settings' dialog, then 'Close' to exit the 'Send/Receive Groups' dialog and return to Outlook.
6. Now whenever you send messages in Outlook using the that account they will show [email protected] as the 'From' address.

Step 6. [Optional] Outlook: Override 'Send Mail as' when desired

1. In the draft message for which you'd like to change the 'Send Mail as' address click on the 'From' button and select 'Other Email Address'
   
2. In the 'Send From Other Email Address' dialog enter any valid 'Send Mail as' address including [email protected]. You can optionally include a display name and in that case the email address should be within angled brackets.  For example:

   blearyeye <[email protected]>
   

   
3. Outlook will include the newly added 'From' address in the list for future emails. You can also delete it from the list.
   

Answer 2

Agree with Jayce's suggestion in the thread you provided. In outlook client, it's suggested that you could configure the two accounts in a profile, so that when you reply to an email, you could click the From field to choose the email address that you want to reply.