Email can not send, Email delivery error: 504 5.7.4 Unrecognized authentication type

I use Exchange Server 2016 as Mail server,
it work fine before IT update mail server's SSL certification.
other AP system on Window Server are okay,
but my redmine failed.
redmine install on Ubuntu 20.04.
log: Email delivery error: 504 5.7.4 Unrecognized authentication type

If anyone could help?

configuration.yml setting as below:

production:
  delivery_method: :smtp
    enable_starttls_auto: true
    port: 587
    domain: "my domain" 
    authentication: :login
    user_name: "account" 
    password: "pwd"

redmine version:

Environment:
  Redmine version                4.2.10.stable
  Ruby version                   2.7.0-p0 (2019-12-25) [x86_64-linux-gnu]
  Rails version                  5.2.8.1
  Environment                    production
  Database adapter               Mysql2
  Mailer queue                   ActiveJob::QueueAdapters::AsyncAdapter
  Mailer delivery                smtp

update:
I don't know why, at last,
use none authentication methond can be send mail.

Replies (3)

RE: Email can not send, Email delivery error: 504 5.7.4 Unrecognized authentication type - Added by salman mp 11 months ago

Test changing authentication: :login to authentication: :plain

RE: Email can not send, Email delivery error: 504 5.7.4 Unrecognized authentication type - Added by Terence Lien 11 months ago

salman mp wrote in RE: Email can not send, Email delivery error: 504 5.7.4 U...:

Test changing authentication: :login to authentication: :plain

Thanks reply,

I tried very combination but not work :(

maybe not redmine config issue but exchange servers'.

RE: Email can not send, Email delivery error: 504 5.7.4 Unrecognized authentication type - Added by Brian BB 10 months ago

First thing I would be checking is the SSL certificates that IT updated on your mail servers. You might need to add a new trusted CA, or import the server certificate.. Hard to say without knowing your setup. But if that was the only change, then the SSL is likely the culprit -- not the SSL itself, but your server needs to accept that SSL as valid.

If the SSL certificate was issued from a new provider (CA - certificate authority), you will have to ensure that new CA is added to your servers trusted CAs.
Since you are using Ubuntu, this will get you started on how you would add a trusted CA to your server

Apart from that, it could be the yml file? I don't see a mail server name there for one...
so maybe:

default:
  email_delivery:
    delivery_method: :smtp
    smtp_settings:
      address: my_mailserver.domain.com
      port: 587
      enable_starttls_auto: true
      domain: my_mail_domain.com     #  mail domain is everything after the @ symbol
      authentication: :login
      user_name: sending_user@my_mail_domain.com
      password: xxxxxxxxxxx

and restart the app.

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