MArtin  writes:
> My headless pi has been sending emails to my normal account from it
> and its companion headless pi for well over a year. They are only
> occasional status, temperature warning and the like so should be well
> under any number or rate limits. With no configuration changes here or
> changes by me to the gmail account it has suddenly stopped working. A
> look at the exim4 log shows the last successful email as:
>
> 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

How is Exim configured? Remote debugging attempts on configuration one
can’t see aren’t very practical.

> Does anyone have any ideas on what google have changed and how to fix
> it? The web page referenced didn't seem to be relevant leastways it
> didn't help me and I can still log into the gmail account on a
> different machine with the credentials in the exim4 configuration.
> Otherwise are their any suggestions on another free account I can get
> to send smtp headless from the pi instead of using google.

Can you see what happens in the SMTP connection? At the least you need
to establish whether Exim is attempting to authenticate and failing, or
not even trying.

Something like:

(echo “To: user@address ; echo Subject: t; echo; echo body) | exim -odf -v -t

--
https://www.greenend.org.uk/rjk/

--- SoupGate-Win32 v1.05