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

[Khalid Baheyeldin]

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> wrote:

> 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.
>>
>
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-- 
Khalid M. Baheyeldin
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