On 10/17/19 4:19 PM, MArtin wrote:
> 2019-10-15 12:59:41 1iKLUK-0008Vq-B4 <= nagios@PI05 H=icinga (PI05)
> [172.18.20.35] P=smtp S=640
> 2019-10-15 12:59:42 1iKLUK-0008Vq-B4 => XXXXXXXX.co.uk
>  R=smarthost T=remote_smtp_smarthost
> H=gmail-smtp-msa.l.google.com [74.125.133.109]
> X=TLS1.2:ECDHE_RSA_CHACHA20_POLY1305:256 CV=no
> DN="C=US,ST=California,L=Mountain View,O=Google LLC,CN=smtp.gmail.com"
> A=plain C="250 2.0.0 OK  1571140782 a10sm21277754wrm.52 - gsmtp"
> 2019-10-15 12:59:42 1iKLUK-0008Vq-B4 Completed
>
> and the first unsuccessful email as:
>
> 2019-10-16 05:15:03 1iKaiE-0001MQ-PH <= nagios@PI05 H=icinga (PI05)
> [172.18.20.35] P=smtp S=529
> 2019-10-16 05:15:04 1iKaiE-0001MQ-PH ** XXXXXXXX.co.uk
>  R=smarthost T=remote_smtp_smarthost H=smtp.gmail.com
> [173.194.76.108] X=TLS1.2:ECDHE_RSA_CHACHA20_POLY1305:256 CV=yes
> DN="C=US,ST=California,L=Mountain View,O=Google
> LLC,CN=smtp.gmail.com": SMTP error from remote mail server after
> pipelined MAIL FROM: SIZE=1568: 530-5.5.1
> Authentication Required. Learn more at\n530 5.5.1
> https://support.google.com/mail/?p=WantAuthError r3sm15957872wre.29 -
> gsmtp

These two logs are non-trivially different to me.  Let's break them down
to what's different (that I think matters).

A)
H=gmail-smtp-msa.l.google.com [74.125.133.109]
CV=no
A=plain
C="250 2.0.0 OK  1571140782 a10sm21277754wrm.52 - gsmtp"

B)
H=smtp.gmail.com [173.194.76.108]
CV=yes: SMTP error from remote mail server after pipelined MAIL
FROM: SIZE=1568: 530-5.5.1 Authentication Required.
Learn more at 530 5.5.1 https://support.google.com/mail/?p=WantAuthError
r3sm15957872wre.29 - gsmtp

1)  H is different.  I would expect them to be the same.
2)  CV is different.  I'm not familiar with exim and can't speak to it.
3)  The first log entry looks like it's using "PLAIN" SMTP
Authentication.  I don't see similar in the second log entry.
4)  The second log entry seems to be complaining about the lack of
authentication, possibly point #3 above.

I hope that point #4 is talking about point #3.  Given that it looks
like you're using IPv4 and not IPv6, you are likely not running into
more stringent requirements that Google enforces on IPv6.

> Does anyone have any ideas on what google have changed and how to fix
> it?

My first guess is that something happened and your client is not trying
to use SMTP Authentication any more.  I have no idea why.

> Any help gratefully received

I don't know if that helps or not.  Hopefully it gives you something to
look at.

For what it's worth, I successfully send email to Google / Gmail daily
from my VPS.  So it is possible to successfully get email into Google,
even as a small email operator.



--
Grant. . . .
unix || die

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