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autoconvert messes up DKIM signature

Path csiph.com!eternal-september.org!feeder.eternal-september.org!.POSTED!not-for-mail
From "Helmut K. C. Tessarek" <kct@evermeet.cx>
Newsgroups comp.mail.sendmail
Subject autoconvert messes up DKIM signature
Date Fri, 31 Oct 2025 17:21:17 -0400
Organization A noiseless patient Spider
Lines 41
Message-ID <10e398f$qf2r$1@dont-email.me> (permalink)
MIME-Version 1.0
Content-Type text/plain; charset=UTF-8; format=flowed
Content-Transfer-Encoding 7bit
Injection-Date Fri, 31 Oct 2025 21:21:20 +0000 (UTC)
Injection-Info dont-email.me; posting-host="e4d774d0b461f7a38889962e8a028f22"; logging-data="867419"; mail-complaints-to="abuse@eternal-september.org"; posting-account="U2FsdGVkX1+39yFgYcLJjnKe4Uqi1fQD"
User-Agent Mozilla Thunderbird
Cancel-Lock sha1:h3s542Tn4sgXrMtDPpdqrWU+kfo=
Content-Language en-US
Xref csiph.com comp.mail.sendmail:8196

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Hello sendmail experts!

Today I sent myself a test email from an updated k9-mail client and imagine my 
surprise as the DKIM check failed with "Invalid (E-mail was modified)".

I checked the mail headers and found the following:

X-MIME-Autoconverted: from quoted-printable to 8bit by [bla] 59VKaHmW832917

Weird, why would sendmail do such a conversion? I never told it to do so (or at 
least I think I never did). I guess k9-mail sent the mail in a format sendmail 
didn't like. However, there is nothing I can do about that. But what is even 
weirder is that sendmail modifies a signed email. So this basically breaks DKIM.

This brought a few interesting questions to light, some of which most likely 
show my non-sendmail-expert status. So please bear with me:

1. Why would sendmail modify the mail after it was signed? Is there a way that 
sendmail does this conversion before the opendkim milter signs it? I can't be 
the only one who uses opendkim and sendmail. Modifying an email after is was 
signed clearly makes no sense.

2. Is there a reason for sendmail to do this conversion in the first place? 
Afaik quoted-printable is not an exotic/unknown format and thus should be 
understood by today's clients.

3. How can I turn off this auto-conversion? Would it result in drawbacks?

While the 3rd one is the brutal approach, I'd rather go with the 1st one, which 
also makes the most sense in terms of a mail processing workflow.
Unfortunately I don't know how to do either.

Here is my sendmail.mc: https://evermeet.cx/paste/sendmail_mc.xD5s.txt 
(available until 2025-11-07 20:56:45 UTC)

Cheers,
   K. C.



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Thread

autoconvert messes up DKIM signature "Helmut K. C. Tessarek" <kct@evermeet.cx> - 2025-10-31 17:21 -0400
  Re: autoconvert messes up DKIM signature "Helmut K. C. Tessarek" <kct@evermeet.cx> - 2025-10-31 19:40 -0400
    Re: autoconvert messes up DKIM signature Marco Moock <mm+solani@dorfdsl.de> - 2025-11-01 10:39 +0100
      Re: autoconvert messes up DKIM signature "Helmut K. C. Tessarek" <kct@evermeet.cx> - 2025-11-01 22:03 -0400
        Re: autoconvert messes up DKIM signature Claus Aßmann <INVALID_NO_CC_REMOVE_IF_YOU_DO_NOT_POST_ml+sendmail(-no-copies-please)@esmtp.org> - 2025-11-02 01:38 -0400

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