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My work's email uses Outlook and I absolutely hate it. I want to use Gmail (previously we had Gmail, but we migrated to Microsoft suite...), it's easy enough to forward all emails to a different account, the problem is that if I reply to any emails, my reply needs to show my [email protected] email address as sender.

Question: Is it possible to reply to emails using a different email address as the sender address?

In specific, I'd like to create a new Gmail account and make it behave as if all emails it receives and sends are received and sent from my work's Outlook account. It seems to be possible, but I'm not really understanding the instructions to be able to say if it definitely is possible: https://www.msoutlook.info/question/578 ; https://social.technet.microsoft.com/forums/office/en-US/7357c6b1-0d08-48f0-87f2-dbac2e61d8fa/reply-to-a-forwarded-email-as-the-original-sender

EDIT: apparently Gmail has this option, for the web version: Go to All Settings, then Email Forwarding etc, Check email from other accounts, Add an email account https://support.google.com/mail/answer/6304825 however, the Gmailify option is disabled and I'm also unable to add manually my work's POP account. (I might have to use unsecure port 110 instead of 995, but I'm afraid of using an unsecure port to send my login credentials)

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  • You notice that you're actually asking how to spoof a from-address in Gmail? Some would call this dubious activity.
    – harrymc
    Sep 20, 2021 at 19:28
  • @harrymc nah the email header would clearly say where it is from.
    – Gantendo
    Sep 20, 2021 at 19:34

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I would seriously recommend caution.

The tools accepted for use at a workplace are determined by the employer, and you have a signed contract where you agree to follow the rules they set. One of them often is using the tools the employer provides.

Using unsanctioned tools can be a serious offense which can lead to immediate termination of contract, and may have possible legal and financial ramifications to boot. An email message can easily be made to look to a layman like being sent from a different account, but it fools any moderately competent IT guy exactly as long as it takes for him to open it.

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  • Thanks for the warning! But I do think in my case it's fine, it's just that the IT department has no idea of how to do it
    – flen
    Sep 20, 2021 at 19:11
  • If the IT department OK:s it, then you indeed should be fine :-) I'm leaving my answer there anyway. You're not the only one who wants / needs to use tools not officially accepted (been there...) and not all of them realize how serious the consequences can be. You usually can specify a reply-to -address but last time I checked I'm pretty sure the sender's address was showing the original account, not the reply-to. Anyway I'd just bite the bullet myself... or use an actual email client instead of webmail; then it makes no difference what's on the backend.
    – Peregrino69
    Sep 20, 2021 at 19:29
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If you use Outlook for desktop, as workaround, you could configure both two accounts into Outlook. No matter which account received the message, you could send or reply as any account from them by changing “From” in Outlook.

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