I can't remember a time when sending to gmail failed to produce a tls connection. I don't wonder if there is a smarthost in between stopping it?

On 10/15/2020 5:23 PM, Jaime Lerner wrote:

An easier place to check is to go to checktls.com to get an excellent output of your mailserver connection and whether it is using TLS.

Might help with trouble-shooting....

*From: *Eric Broch <[email protected]>
*Reply-To: *<[email protected]>
*Date: *Thursday, October 15, 2020 at 5:39 PM
*To: *<[email protected]>
*Subject: *Re: [qmailtoaster] QMT is not issuing a STARTTLS on outbound SMTP

What's this look like

# ls -la /var/qmail/control

On 10/15/2020 2:54 PM, Jim McNamara wrote:

    [root@catchmail2 control]# yum list installed | grep qmail

    qmail.x86_64 1.03-3.3.1.qt.el8 @qmt-testing

    qmailadmin.x86_64 1.2.16-5.1.qt.el8 @qmt-testing

    qmailmrtg.x86_64 4.2-4.qt.el8 @qmt-testing

    On 10/15/20 4:48 PM, Eric Broch wrote:

        What version of qmail?

        On 10/15/2020 2:47 PM, Jim McNamara wrote:

            Received: from mymachine.tld (mymachine.tld. [9.8.7.6])

                    by mx.google.com with ESMTP id

            p5si1775654qvb.199.2020.10.15.09.52.15

                    for <[email protected] <mailto:[email protected]>>;

                    Thu, 15 Oct 2020 09:52:15 -0700 (PDT)

            Received: from mymachine.tld (mymachine.tld. [9.8.7.6])

                    by mx.google.com with ESMTP id

            n10si156346qvl.1.2020.10.15.13.37.49

                    for <[email protected] <mailto:[email protected]>>;

                    Thu, 15 Oct 2020 13:37:49 -0700 (PDT)

            No mention whatsoever of TLS, the next lines of the
            headers begin:

            Received-SPF: pass

            On 10/15/20 3:32 PM, Eric Broch wrote:

                Check the header of an email you've sent to Gmail from
                your QMT,

                you should see something like the following:

                Received: from localhost (mx.mydomain.com.
                [xxx.xxx.xxx.xxx])

                        by mx.google.com with ESMTPS id

                be3si1766151plb.73.2020.10.15.11.34.29

                        for <[email protected]
                <mailto:[email protected]>>

                        (version=TLS1_3 cipher=TLS_AES_256_GCM_SHA384
                bits=256/256);

                I'm sending from a CentOS 8/QMT I just fired up and am
                testing.

                Eric

                On 10/15/2020 12:57 PM, Jim McNamara wrote:

                    Hello, list!

                    According to
                    http://www.qmailtoaster.net/notls.html , all outbound

                    SMTP should be using TLS unless a domain is
                    configured explicitly

                    not use it. However, without even creating the
                    directory

                    /var/qmail/control/notlshosts every message I send
                    from my server

                    to gmail.com is going unencrypted. The
                    /var/log/qmail/send/current

                    file has entries like:

                    2020-10-15 14:29:58.418313500 new msg 8428251

                    2020-10-15 14:29:58.418315500 info msg 8428251:
                    bytes 574 from

                    <[email protected] <mailto:[email protected]>> qp
                    511025 uid 89

                    2020-10-15 14:29:58.418336500 starting delivery 1:
                    msg 8428251 to

                    remote [email protected]
                    <mailto:[email protected]>

                    2020-10-15 14:29:58.418337500 status: local 0/10
                    remote 1/60

                    2020-10-15 14:29:59.220407500 delivery 1: success:

                    <[email protected]
                    
<mailto:[email protected]>>_173.194.204.26_accepted_message./Remote_host_said:_250_2.0.0_OK__1602786599_w13si301qtv.16_-_gsmtp/

                    2020-10-15 14:29:59.220525500 status: local 0/10
                    remote 0/60

                    2020-10-15 14:29:59.220563500 end msg 8428251

                    The message in gmail shows up with the padlock
                    having a red line

                    through it, indicating it was not encrypted during
                    transit. Since

                    I see the 250 in the send log, I would assume that
                    should my

                    server attempt to use TLS, there should be a,
                    "starttls" getting

                    logged?

                    My /var/qmail/supervise/send/run file is simply:

                    #!/bin/sh

                    exec /var/qmail/rc

                    Did I do something wrong that outbound SMTP is not
                    even asking for

                    TLS?

                    
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