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Emacs and Gmail

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  Emacs and Gmail Jonathan Lamothe <jonathan@jlamothe.net> - 2026-04-12 09:56 -0400
    Re: Emacs and Gmail Mekeor Melire <mekeor@posteo.de> - 2026-04-13 16:56 +0200
      Re: Emacs and Gmail Jonathan Lamothe <jonathan@jlamothe.net> - 2026-04-13 12:02 -0400

#61055 — Emacs and Gmail

So I've recently switched to emacs as my primary mail client.  One
problem I'm running into is that when I use it to send mail to a Gmail
address, it invariably ends up in their spam folder.  Sending the same
message from my other clients (FairEmail, neomutt) does not have this
problem.

I've compared the headers and found that mail sent from emacs does not
include an encoding in the Content-Type header.  I don't yet
conclusively know if this is the problem, but I would like to fix it
anyway.  I'm having a hell of a time figuring out how, though.

-- 
Regards,
Jonathan Lamothe
https://jlamothe.net

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#61056

On 2026-04-12 at 09:56, <jonathan@jlamothe.net> wrote:

> So I've recently switched to emacs as my primary mail client.  One
> problem I'm running into is that when I use it to send mail to a Gmail
> address, it invariably ends up in their spam folder.  Sending the same
> message from my other clients (FairEmail, neomutt) does not have this
> problem.
>
> I've compared the headers and found that mail sent from emacs does not
> include an encoding in the Content-Type header.  

Hmm. What about the User-Agent header (`gnus-user-agent')?

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#61057

Mekeor Melire <mekeor@posteo.de> writes:

> On 2026-04-12 at 09:56, <jonathan@jlamothe.net> wrote:
> Hmm. What about the User-Agent header (`gnus-user-agent')?

What's interestng is that neither Gnus, nor my previous client seem to
be sending a User-Agent header, so that can't be the issue.

I've compared the headers from my various clients.

Here are the headers from an email sent from neomutt (not marked spam):

Date: Sat, 11 Apr 2026 23:00:14 +0000
From: Jonathan Lamothe <jonathan@jlamothe.net>
To: [redacted]@gmail.com
Subject: neomutt Test
Message-ID: <20260411230012.tugxwjowwr33q5ai@pertwee.jlamothe.net>
MIME-Version: 1.0
Content-Type: text/plain; charset=us-ascii
Content-Disposition: inline


Here are the headers from an email sent from FairEmail (not marked
spam):

Date: Sat, 11 Apr 2026 20:31:51 +0000
From: Jonathan Lamothe <jonathan@jlamothe.net>
To: [redacted]@gmail.com
Message-ID: <a91451df-dadf-4bca-8d15-2d7f1bdd22c4@jlamothe.net>
Subject: FairEmail Test
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 7bit
X-Correlation-ID: <a91451df-dadf-4bca-8d15-2d7f1bdd22c4@jlamothe.net>


Here are the headers from an email sent from emacs (marked as spam):

From: Jonathan Lamothe <jonathan@jlamothe.net>
To: [redacted]@gmail.com
Subject: Emacs Test
Date: Sat, 11 Apr 2026 20:46:09 +0000
Message-ID: <874ilh6x9t.fsf@posteo.de>
MIME-Version: 1.0
Content-Type: text/plain


Things I've unsuccessfully tried:

- Hacknig emacs to change the Message-ID so that the part before the @
  is a SHA256
- Ensuring that the Content-Type header contais an encoding i.e.:
  text/plain; charset=UTF-8

Also worth noting: replies sent to email originating from Gmail seem to
be passing the spam filter.

-- 
Regards,
Jonathan Lamothe
https://jlamothe.net

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