Can't send emails using outlook365

Installation Issues
1

Hello,

I am trying to send mails via outlook365, which fails with:

docker-compose exec passbolt su -m -c "/usr/share/php/passbolt/bin/cake \
                                passbolt send_test_email --recipient=test@example.org --verbose" -s /bin/sh www-data
                                
                                
-------------------------------------------------------------------------------
 Debug email shell
-------------------------------------------------------------------------------
Email configuration
-------------------------------------------------------------------------------
Host: smtp.office365.com
Port: 587
Username: test123@example.org
Password: *********
TLS: true
Sending email from: Passbolt <test123@example.org>
Sending email to: test@example.org
-------------------------------------------------------------------------------
Trace
[220] AS9PR06CA0023.outlook.office365.com Microsoft ESMTP MAIL Service ready at Wed, 16 Mar 2022 11:15:51 +0000
> EHLO localhost
[250] AS9PR06CA0023.outlook.office365.com Hello [1.2.3.4]
[250] SIZE 157286400
[250] PIPELINING
[250] DSN
[250] ENHANCEDSTATUSCODES
[250] STARTTLS
[250] 8BITMIME
[250] BINARYMIME
[250] CHUNKING
[250] SMTPUTF8
> STARTTLS
[220] 2.0.0 SMTP server ready
> EHLO localhost
[250] AS9PR06CA0023.outlook.office365.com Hello [1.2.3.4]
[250] SIZE 157286400
[250] PIPELINING
[250] DSN
[250] ENHANCEDSTATUSCODES
[250] AUTH LOGIN XOAUTH2
[250] 8BITMIME
[250] BINARYMIME
[250] CHUNKING
[250] SMTPUTF8
> AUTH PLAIN xxx*****
[504] 5.7.4 Unrecognized authentication type [AS9PR06CA0023.eurprd06.prod.outlook.com]
> AUTH LOGIN
[334] xxx
> *****
[334] xxx
Could not send the test email.
Error: SMTP server did not accept the password.

This is the docker-compose.yml:

version: '3.7'
services:
  db:
    image: mariadb:10.7.1
    restart: unless-stopped
    environment:
      MYSQL_RANDOM_ROOT_PASSWORD: "true"
      MYSQL_DATABASE: "passbolt"
      MYSQL_USER: "passbolt"
      MYSQL_PASSWORD: "xxx"
    volumes:
      - database_volume:/var/lib/mysql

  passbolt:
    image: passbolt/passbolt:3.5.0-ce
    restart: unless-stopped
    tty: true
    depends_on:
      - db
    environment:
      APP_FULL_BASE_URL: https://passbolt.example.org
      DATASOURCES_DEFAULT_HOST: "db"
      DATASOURCES_DEFAULT_USERNAME: "passbolt"
      DATASOURCES_DEFAULT_PASSWORD: "xxx"
      DATASOURCES_DEFAULT_DATABASE: "passbolt"
      EMAIL_DEFAULT_FROM: "test123@example.org"
      EMAIL_TRANSPORT_DEFAULT_HOST: "smtp.office365.com"
      EMAIL_TRANSPORT_DEFAULT_PORT: 587
      EMAIL_TRANSPORT_DEFAULT_TLS: "true"
      EMAIL_TRANSPORT_DEFAULT_USERNAME: "test123@example.org"
      EMAIL_TRANSPORT_DEFAULT_PASSWORD: "xxx"
    volumes:
      - gpg_volume:/etc/passbolt/gpg
      - jwt_volume:/etc/passbolt/jwt
    command: ["/usr/bin/wait-for.sh", "-t", "0", "db:3306", "--", "/docker-entrypoint.sh"]
    networks:
      - traefik_web
      - default
    
    volumes:
  database_volume:
    driver: local
  gpg_volume:
    driver: local
  jwt_volume:
    driver: local
networks:
  traefik_web:
    external: true

The credentials are working fine on a GitLab-server running with docker, so I don’t see the problem here.

2

Hi @ahoi Welcome to the forum! Is your Outlook 2FA enabled? An Outlook app password might be needed to bypass it?

1 Like
3

Hi and thank you for your answer :slight_smile:

That was the solution. So obvious, but as I don’t manage the outlook365-stuff I did not see it.

Thanks!

1 Like