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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 [email protected]

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 <[email protected]>... Connecting to local...
050 <[email protected]>... 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

asked Jul 29, 2019 at 22:25
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  • 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. Commented Jul 30, 2019 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) Commented Jul 30, 2019 at 15:25

1 Answer 1

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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

answered Jul 29, 2019 at 22:44
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  • I wondered that, a bit more research I found ssmtp doesn't seem to have been updated in a good few years Commented Jul 29, 2019 at 23:03

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