Saturday, January 17, 2015

Email fun: 8BITMIME and DKIM body authentication failure

Like most of you who decided to read this post, we use DomainKeys Identified Mail (DKIM) in an attempt to keep email spoofing down. . We noticed that some of the emails we were receiving were marked as spam by spamassassin when they shouldn't. Looking at the email header we saw they were failing the DKIM body integrity test. The entries in the header file looks something like

Authentication-Results (amavisd-new); dkim=softfail 
(fail, body has been altered)
dkim=neutral (body hash did not verify).
dkim=fail (message has been altered) domainkeys=pass

That would increase the score of those legitimate emails just above the threshold, causing spamassassin to flag them as spam. After some investigating, we found out emails that contained characters above the original ASCII character set, such as Olivenöl, in the body of the message were failing. In other words, DKIM really does not like 8bit (specifically 8BITMIME) encoding.

I was able to duplicate that by sending an email to myself or to a gmail test account using our default mail client, Thunderbird. So I tried to manually (using netcat; telnet would have worked fine) create a properly configured 8Bit email using our SMTP server (As you can clearly see, our MX server (postfix) is setup to handle 8BITMIME):

raub@desktop:/tmp$ nc -t 25
220 Test Mail Server
250 DSN
250 2.1.0 Ok
250 2.1.5 Ok
354 End data with <CR><LF>.<CR><LF>
From: "Mauricio Tavares" 
Subject: 8bit test
Date: Mon, 30 Jun 2014 11:10:05 -0400
MIME-Version: 1.0
Content-Transfer-Encoding: 8bit


250 2.0.0 Ok: queued as 2BA1F80041
221 2.0.0 Bye

The above would work while using Thunderbird didn't. After setting Thunderbird to debug mode, we noticed it was not properly indicating the email was 8BITMIME, so postfix would treat it as a 7bit ASCII email and then DKIM would fail. The DKIM signatures of 8BITMIME mail may break unless all SMTP servers in the path implement and announce 8BITMIME support, and as shown above the mail clients do not lie. Since we cannot guarantee that is the case, it is better to down-convert to quoted-printable before DKIM signing.

Solution is to force the MTA to downconvert to 7bit. That can be done in postfix by creating a null filter in that is called before the rest of the filters. In other words, something like

smtp      inet  n       -       n       -       -       smtpd
   -o content_filter=smtp-downconvert:
smtp-downconvert  unix    -       -       -       -       2       smtp
   -o smtp_discard_ehlo_keywords=8bitmime,silent-discard inet  n       -       n       -       -       smtpd
   -o smtpd_authorized_xforward_hosts=
   -o smtpd_client_restrictions=
   -o smtpd_helo_restrictions=
   -o smtpd_sender_restrictions=
   -o smtpd_relay_restrictions=
   -o smtpd_recipient_restrictions=permit_mynetworks,reject

should do the trick. If we restart the MX (postfix reload will do the trick) and send the test email again, the email now should show something like

Authentication-Results (amavisd-new); dkim=pass

in the header, which means DCKIM is successful and life is good... for now

I would like to thank Wietse Venema for pointing me on the right direction regarding downconverting.

Note: HELO vs EHLO

  • HELO: Standard/Original SMTP (7-bit ASCII email) (RFC 821, 5321)
  • EHLO: ESMTP (RFC 1869). Think Enhanced HELO; supports MIME and other exciting extensions. A quick discussion is found at

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