1445823 - office 365 SMTP issue -> failed AUTH: Command unknown: 'AUTH'

Status: UNCONFIRMED

(Bugzilla :: Email Notifications, defect)

Description

[silergy.bugzilla]

User Agent: Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/64.0.3282.186 Safari/537.36

Steps to reproduce:

I am using Bugzilla version 5.0.4. Setting SMTP as given at http://bugzilla.readthedocs.io/en/latest/installing/essential-post-install-config.html#use-another-mail-server 
Setting at administration->parameters->email:
smtpserver : ip address with port for the office 365 SMTP server (valid)
smtp_username : a valid user id
smtp_password : valid password for the user id
smtp_ssl : off

Update or log any bug, I get an error as:
There was an error sending mail from '[e-mail]' to '[e-mail]': failed AUTH: Command unknown: 'AUTH' 

I tried with 
smtp_ssl : on 
as well.

In that case, I get following error:
There was an error sending mail from '[e-mail]' to '[e-mail]': unable to establish SMTP connection to <<smtp_ip>> port <<smtp_port>> 



Actual results:

When I use Gmail configuration as given at 
http://bugzilla.readthedocs.io/en/latest/installing/essential-post-install-config.html#gmail I don't get the error and email go through.

So, please share how to set office 365 SMTP with Bugzilla 5.0.4.

Comment 1

[Oniel]

set
smtp_ssl:on

then edit Mailer.pm and in the if($method eq "SMTP") you should replace:

ssl => Bugzilla->params->{'smtp_ssl'},

with

$port eq "587" ? (ssl => "starttls") : (ssl => Bugzilla->params->{'smtp_ssl'}),

Comment 2

[arthurborsboom]

Sending mails using Microsoft 365 fails probably due to STARTTLS.
SMTP information from Microsoft, source: https://support.microsoft.com/en-us/office/pop-imap-and-smtp-settings-8361e398-8af4-4e97-b147-6c6c4ac95353

• SMTP hostname: smtp.office365.com
• Port: 587
• Encryption: STARTTLS

I confirm that the suggested change fixes the mail problem for me.
To be more precise, this is the file I changed.

/srv/http/bugzilla/Bugzilla/Mailer.pm

This has been the result after the replace, where the old ssl line has been commented out.

  if ($method eq "SMTP") {
    my ($host, $port) = split(/:/, Bugzilla->params->{'smtpserver'}, 2);
    $transport = Bugzilla->request_cache->{smtp}
      //= Email::Sender::Transport::SMTP::Persistent->new({
      host => $host,
      defined($port) ? (port => $port) : (),
      sasl_username => Bugzilla->params->{'smtp_username'},
      sasl_password => Bugzilla->params->{'smtp_password'},
      helo          => $hostname,
      # ssl           => Bugzilla->params->{'smtp_ssl'},
      $port eq "587" ? (ssl => "starttls") : (ssl => Bugzilla->params->{'smtp_ssl'}),
      debug         => Bugzilla->params->{'smtp_debug'}
      });
  }

If this is the correct fix, then it would be nice to have this included in the next Bugzilla release.