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  • Emacs and Gmail

    From Jonathan Lamothe@jonathan@jlamothe.net to gnu.emacs.help on Sun Apr 12 09:56:13 2026
    From Newsgroup: gnu.emacs.help

    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
    --- Synchronet 3.21f-Linux NewsLink 1.2
  • From Mekeor Melire@mekeor@posteo.de to gnu.emacs.help on Mon Apr 13 16:56:55 2026
    From Newsgroup: gnu.emacs.help

    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')?
    --- Synchronet 3.21f-Linux NewsLink 1.2
  • From Jonathan Lamothe@jonathan@jlamothe.net to gnu.emacs.help on Mon Apr 13 12:02:47 2026
    From Newsgroup: gnu.emacs.help

    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
    --- Synchronet 3.21f-Linux NewsLink 1.2