On Mon, Apr 06, 2020 at 08:21:32AM +0100, Dominic Raferd wrote:

> Using setting 'smtp_tls_security_level = may' (postfix 3.3.0) is there
> a reliable way to see from log which outgoing emails were sent in the
> clear i.e. *not* using TLS?

Yes, provided you don't lose too many log messages[1], and your logging
subsystem does not reorder them[1], set:

    smtp_tls_loglevel = 1

and use "collate":

    https://github.com/vdukhovni/postfix/tree/master/postfix/auxiliary/collate

whose output you'd send to the attached Perl script.  On my system for
example:

    # bzip2 -dcf $(ls -tr /var/log/maillog*) | perl collate | perl tlstype.pl

-- 
    Viktor.

[1] If your system is suffering under the yoke of systemd-journald, you
should strongly consider enabling the built-in logging in recent
versions of Postfix to bypass systemd's broken logging subsystem.

    - It is single-threaded, performs poorly on multi-cpu servers and
      may not be able to keep up with all the messages generated on a
      busy multi-cpu system.

    - By default has low message rate limits, dropping messages
      that exceed the limits.

    - Listens on stream socket rather than a dgram socket, which
      breaks message ordering from multi-process systems like
      Postfix.
#! /usr/bin/env perl

use strict;
use warnings;

local $/ = "\n\n";

while (<>) {
    my $qid;
    my %tls;
    my $smtp;
    foreach my $line (split("\n")) {
	if ($line =~ m{ postfix(?:\S*?)/qmgr\[\d+\]: (\w+): from=<.*>, size=\d+, nrcpt=\d+ [(]queue active[)]$}) {
	    $qid //= $1;
	    next;
	}
	if ($line =~ m{ postfix(?:\S*?)/smtp\[(\d+)\]: (\S+) TLS connection established to (\S+): (.*)}) {
	    $tls{$1}->{$3} = [$2, $4];
	    next;
	}
	if ($line =~ m{.*? postfix(?:\S*?)/smtp\[(\d+)\]: (\w+): (to=.*), relay=(\S+), (delay=\S+, delays=\S+, dsn=2\.\S+, status=sent .*)}) {
	    next unless $qid eq $2;
	    if (defined($tls{$1}->{$4}) && ($tls{$1}->{$4}->[2] //= $5) eq $5) {
		printf "qid=%s, relay=%s, %s -> %s %s\n", $qid, $4, $3, @{$tls{$1}->{$4}}[0..1];
	    } else {
		delete $tls{$1};
		printf "qid=%s, relay=%s, %s -> cleartext\n", $qid, $4, $3;
	    }
	}
    }
}

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