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I've configured SSMTP on my Raspberry Pi (Pi 4 with latest Raspbian), it appears to mostly be configured correctly however when I run the command

echo -n 'Subject: test\n\nTesting ssmtp' | sendmail -v tousername@example.com

to send verify the message, I get this response:

050 550-5.7.1 [2a00:23c7:688e:700:ca02:b77b:23b8:ef02] Our system has detected that
050 550-5.7.1 this message does not meet IPv6 sending guidelines regarding PTR
050 550-5.7.1 records and authentication. Please review
050 550-5.7.1  https://support.google.com/mail/?p=IPv6AuthError for more information
050 550 5.7.1 . d7si66897775wrc.231 - gsmtp
050 <laurence@pi4.home>... Connecting to local...
050 <laurence@pi4.home>... Sent
250 2.0.0 x6TMB1ha004357 Message accepted for delivery

and I don't receive the message (even though one of the lines states 'message accepted for delivery').

Any ideas how I can resolve this? Obviously this is only an internal device on my home network so it doesn't have a domain associated with it as such.

I do have my own domain and everything related to that is redirected to G-suite business so that is a possibility, but I'm hoping to set this up with just the personal Gmail account.

I've used multiple sites for config instructions however this seems to be authoritative: https://wiki.archlinux.org/index.php/SSMTP

  • Raspberry Pi is irrelevant to this question. This probably should go to Google support. They do not allow you to relay through their servers unconditionally. Check their documentation. – Brick Jul 30 '19 at 2:43
  • @Brick yep I realise that, which is why I'm authenticating (and the limits are in the thousands even for private accounts) – laurencemadill Jul 30 '19 at 15:25
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ssmtp has been deprecated in Debian Buster.

I believe it is possible to configure, but requires significant changes.

Try msmtp instead.

See https://raspberrypi.stackexchange.com/a/100704/8697

| improve this answer | |
  • I wondered that, a bit more research I found ssmtp doesn't seem to have been updated in a good few years – laurencemadill Jul 29 '19 at 23:03

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