Redmine

Hi,

We've recently configured Redmine for our organization, and while everything seems to be working smoothly, we're encountering an issue with email notifications.

We have configured the email delivery method to use SMTP, as shown below:

email_delivery:
  delivery_method: :smtp
    smtp_settings:
      address: smtp.office365.com
      port: 587
      domain: smtp.office365.com
      authentication: :login
      user_name: "noreply@myorg.com" 
      password: "my~p@ssw0rd" 
      enable_starttls_auto: true

However, when attempting to send a test email, we receive the following error:

An error occurred while sending mail (535 5.7.139 Authentication unsuccessful, basic authentication is disabled. [BM1PR01CA0164.INDPRD01.PROD.OUTLOOK.COM 2024-02-28T11:48:49.884Z 08DC38275E4F25C6])

Our research suggests that Redmine may not fully support modern authentication methods by default, and Microsoft's deprecation of basic authentication for Office 365 further complicates this situation.

We would greatly appreciate your guidance on how to address this issue and ensure successful email notifications from Redmine.

Below are the Redmine installation information.

Environment:
  Redmine version                5.0.3.stable
  Ruby version                   2.6.10-p210 (2022-04-12) [x64-mingw32]
  Rails version                  6.1.7
  Environment                    production
  Database adapter               Mysql2
  Mailer queue                   ActiveJob::QueueAdapters::AsyncAdapter
  Mailer delivery                smtp
Redmine settings:
  Redmine theme                  Default
SCM:
  Git                            2.41.0
  Filesystem                     
Redmine plugins:
  no plugin installed

Thank you for your time and assistance.