[kwlug-disc] msmtp email to gmail not landing - ideas?

[B. S.]

Yes. Thus that test.

Never mind 465. There's a 'tls_starttls off' directive that causes 
things to ssl from the get go. (Rather than sending a separate starttls 
command.) Once set, sends to 465 just worked.


On 03/30/2017 12:35 PM, Khalid Baheyeldin wrote:
> Does the Thunderbird message gets handed to indieserve as well?
>
> Can you ask them to look at the log for you?
>
> On Thu, Mar 30, 2017 at 12:30 PM, B.S. <bs27975.2 at gmail.com
> <mailto:bs27975.2 at gmail.com>> wrote:
>
>     The message gets handed off to cpanel2.indieserve.net
>     <http://cpanel2.indieserve.net> in all cases just fine, returning
>     '250 OK'. There is no log for me to see.
>
>     I fired up an identity in Thunderbird, and it's able to send to
>     gmail just fine (same smtp server).
>
>     Curiously, however, the identity is using port 465. While the debian
>     machine, both port 25 and port 587 work just fine, port 465 just
>     times out.
>
>     I'm guessing msmtp (sendmail replacement) isn't sending an initial
>     ssl handshake that 465 is waiting for.
>
>     I don't know if ssl/465 would capture any magic that would
>     facilitate forwarding on to gmail. Probably nothing to do with the
>     problem.
>
>
>     On 03/30/2017 12:15 PM, Khalid Baheyeldin wrote:
>
>         I don't know gsmtp, but I do have postfix sending emails to gmail
>         without issues.
>
>         It could be PTR not set for your server, it could be DKIM, or
>         plain old
>         SPF for your domain.
>
>         Start by looking in the logs. Here is a successful send from
>         Nagios (a
>         monitoring platform) to a Gmail address:
>
>         Mar 29 16:11:01 mon postfix/pickup[20500]: 383FF3A0EF: uid=113
>         from=<nagios>
>         Mar 29 16:11:01 mon postfix/cleanup[31256]: 383FF3A0EF:
>         message-id=<20170329201101.383FF3A0EF at server.example.com
>         <mailto:20170329201101.383FF3A0EF at server.example.com>
>         <mailto:20170329201101.383FF3A0EF at server.example.com
>         <mailto:20170329201101.383FF3A0EF at server.example.com>>>
>         Mar 29 16:11:01 mon postfix/qmgr[4082]: 383FF3A0EF:
>         from=<nagios at example.com <mailto:nagios at example.com>
>         <mailto:nagios at example.com <mailto:nagios at example.com>>>,
>         size=644, nrcpt=1
>         (queue active)
>         Mar 29 16:11:01 mon postfix/smtp[31258]: 383FF3A0EF:
>         to=<myaddress at gmail.com <mailto:myaddress at gmail.com>
>         <mailto:myaddress at gmail.com <mailto:myaddress at gmail.com>>>,
>         relay=gmail-smtp-in.l.google.com <http://gmail-smtp-in.l.google.com>
>         <http://gmail-smtp-in.l.google.com
>         <http://gmail-smtp-in.l.google.com>>[209.85.201.26
>         <tel:%5B209.85.201.26>]:25, delay=0
>         .55, delays=0.02/0.01/0.11/0.41, dsn=2.0.0, status=sent (250
>         2.0.0 OK
>         1490818251 o129si7061411qkc.290 - gsmtp)
>         Mar 29 16:11:01 mon postfix/qmgr[4082]: 383FF3A0EF: removed
>
>
>         On Thu, Mar 30, 2017 at 12:00 PM, B.S. <bs27975.2 at gmail.com
>         <mailto:bs27975.2 at gmail.com>
>         <mailto:bs27975.2 at gmail.com <mailto:bs27975.2 at gmail.com>>> wrote:
>
>              So on a Debian Jessie machine, I'm trying to get system
>         notification
>              mail messages out to real e-mail so I actually find out
>         something
>              happened. Like an unattended-upgrade failure.
>
>              I understand that default installs auto install localhost mail
>              facilities only. So I've installed msmtp and it's largely
>         entirely
>              working.
>
>              However, e-mail to gmail accounts never seem to land.
>         @live.ca <http://live.ca>
>              <http://live.ca> just works, instantly even. Yahoo and another
>              non-gmail provider too.
>
>              In all cases, cpanel2.indieserve.net
>         <http://cpanel2.indieserve.net> <http://cpanel2.indieserve.net>
>              swallows up the message without error.
>
>              Just nothing ever arrives when sent to @gmail.com
>         <http://gmail.com> <http://gmail.com>.
>
>              Anyone have any ideas?
>
>              Or is this something needing configuration on
>         mail.kwlug.org <http://mail.kwlug.org>
>              <http://mail.kwlug.org>, like DKIM, or some other bizarreness?
>
>              Thanks for any thoughts.
>
>
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>
>
>
> --
> Khalid M. Baheyeldin
> 2bits.com <http://2bits.com>, Inc.
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