SMTP for group : ssl wrong version number error

Configuration is rather classic : usual 587 port and starttls is true (default value)

general configuration :

for group smtp :

I’ve been doing some tcpdump to see whats going on and I’m noticing 3 different behaviors. For the first two cases, it’s exactly as described in this thread.

  1. Normal usage

Users creates topics, responds, etc. other users receive email notifications as expected
Also, using the test send email through the administration interface : no problem it’s well sent and well received

with tcpdump we can see there is a correct sequence, connecting through STARTTLS, etc.

  1. Discourse-doctor and rake

using discourse-doctor or rake emails:test
Email is not sent and I have an error : 503 5.5.1 Invalid command: Command not supported

  1. group smtp

When testing the group smtp, I see a “DATA fragment” packet coming from Discourse immediatly after the tcp handshake, to which the smtp server responds with 220 xxxxxxx ESMTP OpenSMTPD followed by a 500 5.5.1 Invalid command: Pipelining not supported message

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