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Relayed emails come 'from' me@gmail.com, not sender@theirdomain.com, so I cannot reply.

I have several domains and am using Postfix to relay emails sent to me@mydomains.com on to me@gmail.com as outlined in Your own mail server with Postfix leveraging Gmail as storage (via smtp.gmail.com). I have additionally set up Gmail aliases to send emails as me@mydomains.com and it almost all works brilliantly. However, I cannot reply to emails in my Gmail inbox, sent to my aliases, as the 'from' information gets overwritten with my Gmail email address instead of that of the actual sender.

Is it possible to ensure the sender's email address propagates in the relay or is this the stage where I have to buy a Workspace subscription?

Megalomatt
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Gmail and many mail services do this for obvious spam reasons. Gmail is not legitimate to send emails "From: sender@theirdomain.com" if the owner of theirdomain.com has not explicitly allowed Gmail to do that that (through SPF by instance), and if it did, it is only for its own purpose, not for other Gmail users (you). This is seen as sender spoofing.

A Workspace subscription will permit you to send emails "From: you@yourdomain.com" if you own yourdomain.com and you have got it verified, but you will still be unable to send emails "From: user@otherdomain.com".

You should use the "Reply-to" header in your case.

Dylan
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  • Thank you, however, I think you misread the question. I do not want to send emails as sender@theirdomain.com, I want to reply to them. – Megalomatt Apr 11 '23 at 01:07
  • You need a postfix rule to put the initial From value into the Reply-to header before sending the mail to Gmail's servers. – Dylan Apr 12 '23 at 08:44