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

[B.S.]

The message gets handed off to 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>>
> Mar 29 16:11:01 mon postfix/qmgr[4082]: 383FF3A0EF:
> from=<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>>,
> relay=gmail-smtp-in.l.google.com
> <http://gmail-smtp-in.l.google.com>[209.85.201.26]: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>> 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> just works, instantly even. Yahoo and another
>     non-gmail provider too.
>
>     In all cases, 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>.
>
>     Anyone have any ideas?
>
>     Or is this something needing configuration on mail.kwlug.org
>     <http://mail.kwlug.org>, like DKIM, or some other bizarreness?
>
>     Thanks for any thoughts.