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"Reply-to" appears to be working incorrectly (?)

#1571

Hi Benny,

I have two email addresses a@mydomain.com and b@gmail.com. The mydomain address is for work; the Gmail address is personal; the server that manages my work email auto-forwards emails addressed to "a@mydomain.com" to my Gmail account, and I have Gmail filters separate it all back out again. (It's a little screwy, but it allows me to take advantage of Gmail's spam filtering and global search, and that turns out to be useful.)

I have observed that when I send email from a@mydomain.com, and someone replies to it, the reply is addressed to b@gmail.com, which is emphatically not what I want, and I can't find a way to change the behavior. It's as though the reply-to header is always set to "b@gmail.com" independent of the address from which I sent the message (and indeed, that might be exactly what is going on. Unfortunately, I haven't yet figured out how to examine the full headers of my own emails in order to better diagnose this issue).

The behavior I would like is that mail sent from "a@mydomain.com" has its reply-to set to "a@mydomain.com" and that mail sent from "b@gmail.com" has its reply-to set to "b@gmail.com".

How might I accomplish this?

To be clear, I think my question is as simple as "how can I set the Reply-to header to always be the same as the From header?"
...but perhaps the situation is more complicated than I realize (e.g. due to Google's non-standard IMAP implementation).

On a related side note, if you could help me examine the email's full headers, I would be delighted to give additional information.

Thanks in advance!
Wes

PS please note that this report may be related to report #1366.

Reported by Wes Carroll · November 10th, 2016 @ 06:03 AM

State: resolved
Milestone: none
Assigned to: benny benny

Activity

  1. benny
    benny
    • State changed from new to resolved
    • You can use ⌥⌘U to view the raw message and all of its headers.
    • If you send through Gmail SMTP then Google might alter your From address. (Which I consider to be really bad -- it would be better if they simply rejected sending.)
    • MailMate does not set a reply-to header. It's the From header which controls what happens when people reply to your emails.
    • Earlier on, Gmail could be told to accept other From addresses, but I'm not quite sure this is still possible. Seems you need another SMTP server to do this.

    One workaround would be to setup a second Gmail account for your alternative domain. Then configure it with the SMTP server of the work domain if you have access to that for your work email (it would just be used to submit messages). That way, no-one can see that you are using a Gmail account to receive/store your emails.

    Let me know if this does not resolve your issue.

    November 10th, 2016 @ 11:27 AM

  2. Wes Carroll
    Wes Carroll

    Received and understood. I will report back. Thanks so much!

    November 11th, 2016 @ 03:06 AM

  3. Wes Carroll
    Wes Carroll

    My issue was resolved by switching my work email to Fastmail (per your suggestion); indeed Gmail has changed the way it handles outgoing mail in this case.

    Mailmate has performed admirably, as always. Thank you as well for the help in finding the raw message; this helped me to dispatch a few small setup issues that came up along the way.

    November 24th, 2016 @ 05:28 AM

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