Gitlab SMTP shows "Net::SMTPAuthenticationError: 503 5.5.1 Error: authentication not enabled"

Marslo Jiao

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Mar 7, 2017, 10:49:21 AM3/7/17

to GitLab

The mail account and password works in our JIRA and Confluence, but it just cannot work in my environment. I've check online and tried about 1 week, but still cannot find the solution. May I know what's wrong?

Thanks.

The /etc/gitlab/gitlab.rb:

gitlab_rails['smtp_enable'] = true

gitlab_rails['smtp_address'] = 'smtp.company.com'

gitlab_rails['smtp_port'] = 25

gitlab_rails['smtp_user_name'] = 'my....@company.com'

gitlab_rails['smtp_password'] = 'password'

gitlab_rails['smtp_domain'] = 'company.com'

# gitlab_rails['smtp_authentication'] = 'login' or 'plain'

gitlab_rails['smtp_authentication'] = 'plain'

gitlab_rails['smtp_enable_starttls_auto'] = true

gitlab_rails['smtp_tls'] = false

gitlab_rails['smtp_openssl_verify_mode'] = 'none'

/opt/gitlab/embedded/service/gitlab-rails/config/environments/production.rb:

# config.action_mailer.delivery_method = :sendmail

config.action_mailer.delivery_method = :smtp

config.action_mailer.perform_deliveries = true

config.action_mailer.raise_delivery_errors = true

config.eager_load = true

config.allow_concurrency = false

The test command shows:

> Notify.test_email('marsl...@company.com', 'Message Subject', 'Message Body').deliver_now

Notify#test_email: processed outbound mail in 1.3ms

Sent mail to marsl...@company.com (685.6ms)

Date: Tue, 07 Mar 2017 23:24:36 +0800

From: GitLab <my....@company.com>

Reply-To: GitLab <my....@philips.com>

To: marsl...@company.com

Message-ID: <58bed0b46c4d4_1dc...@Gitlab.mail>

Subject: Message Subject

Mime-Version: 1.0

Content-Type: text/html;

charset=UTF-8

Content-Transfer-Encoding: 7bit

<!DOCTYPE html PUBLIC "-//W3C//DTD HTML 4.0 Transitional//EN" "http://www.w3.org/TR/REC-html40/loose.dtd">

<html><body><p>Message Body</p></body></html>

Net::SMTPAuthenticationError: 503 5.5.1 Error: authentication not enabled

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:977:in `check_auth_response'

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:741:in `auth_plain'

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:733:in `authenticate'

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:568:in `do_start'

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:521:in `start'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/mail-2.6.4/lib/mail/network/delivery_methods/smtp.rb:113:in `deliver!'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/mail-2.6.4/lib/mail/message.rb:2149:in `do_delivery'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/mail-2.6.4/lib/mail/message.rb:237:in `block in deliver'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/actionmailer-4.2.7.1/lib/action_mailer/base.rb:543:in `block in deliver_mail'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/activesupport-4.2.7.1/lib/active_support/notifications.rb:164:in `block in instrument'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/activesupport-4.2.7.1/lib/active_support/notifications/instrumenter.rb:20:in `instrument'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/activesupport-4.2.7.1/lib/active_support/notifications.rb:164:in `instrument'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/actionmailer-4.2.7.1/lib/action_mailer/base.rb:541:in `deliver_mail'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/mail-2.6.4/lib/mail/message.rb:237:in `deliver'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/actionmailer-4.2.7.1/lib/action_mailer/message_delivery.rb:85:in `deliver_now'

from (irb):2

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/railties-4.2.7.1/lib/rails/commands/console.rb:110:in `start'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/railties-4.2.7.1/lib/rails/commands/console.rb:9:in `start'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/railties-4.2.7.1/lib/rails/commands/commands_tasks.rb:68:in `console'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/railties-4.2.7.1/lib/rails/commands/commands_tasks.rb:39:in `run_command!'

from /opt/gitlab/embedded/service/gem/ruby/2.3.0/gems/railties-4.2.7.1/lib/rails/commands.rb:17:in `<top (required)>'

from bin/rails:9:in `require'

from bin/rails:9:in `<main>'

irb(main):003:0> exit

Marslo Jiao

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Mar 7, 2017, 10:52:12 AM3/7/17

to GitLab

Here my environment:

* OS: Ubuntu 16.04 LTS

* Gitlab: 8.15.4

* git version 2.7.4

Marslo Jiao

unread,

Mar 15, 2017, 1:01:40 PM3/15/17

to GitLab

Anyone can help me?

Thanks in advanced.

On Tuesday, March 7, 2017 at 11:49:21 PM UTC+8, Marslo Jiao wrote:

The mail account and password works in our JIRA and Confluence, but it just cannot work in my environment. I've check online and tried about 1 week, but still cannot find the solution. May I know what's wrong?
Thanks.

The /etc/gitlab/gitlab.rb:
gitlab_rails['smtp_enable'] = true
gitlab_rails['smtp_address'] = 'smtp.company.com'
gitlab_rails['smtp_port'] = 25
gitlab_rails['smtp_user_name'] = 'my....@company.com'
gitlab_rails['smtp_password'] = 'password'
gitlab_rails['smtp_domain'] = 'company.com'
# gitlab_rails['smtp_authentication'] = 'login' or 'plain'
gitlab_rails['smtp_authentication'] = 'plain'
gitlab_rails['smtp_enable_starttls_auto'] = true
gitlab_rails['smtp_tls'] = false
gitlab_rails['smtp_openssl_verify_mode'] = 'none'

/opt/gitlab/embedded/service/gitlab-rails/config/environments/production.rb:
# config.action_mailer.delivery_method = :sendmail
config.action_mailer.delivery_method = :smtp
config.action_mailer.perform_deliveries = true
config.action_mailer.raise_delivery_errors = true
config.eager_load = true
config.allow_concurrency = false

The test command shows:

> Notify.test_email('marslo.ji...@company.com', 'Message Subject', 'Message Body').deliver_now

Notify#test_email: processed outbound mail in 1.3ms

Sent mail to marsl...@company.com (685.6ms)
Date: Tue, 07 Mar 2017 23:24:36 +0800
From: GitLab <my....@company.com>
Reply-To: GitLab <my....@philips.com>
To: marsl...@company.com

Message-ID: <58bed0b46c4d4_1dce3fdc836db1146863@Gitlab.mail>

Magnus Therning

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Mar 16, 2017, 5:03:35 AM3/16/17

to gitl...@googlegroups.com

Marslo Jiao <marsl...@gmail.com> writes:

> Anyone can help me?
> Thanks in advanced.

My suggestion is that you also check the mail server logs, maybe they
can shed more light on the issue.

/M

--
Magnus Therning, magnus....@cipherstone.com
Cipherstone Technologies AB
Theres Svenssons gata 10, 417 55 Gothenburg, Sweden

Unix is the answer, but only if you phrase the question very
carefully.
— Unknown

Message has been deleted

Marslo Jiao

unread,

Apr 24, 2017, 8:03:38 AM4/24/17

to GitLab

After the gitlab_rails['smtp_tls'] = false set to gitlab_rails['smtp_tls'] = true

The error shows to OPENSSL error, but still haven't any clue about it.

irb(main):001:0> Notify.test_email('marsl...@mycompany.com', 'test subject', 'test body').deliver_now

Notify#test_email: processed outbound mail in 408.9ms

Sent mail to marsl...@mycompany.com (545.2ms)

Date: Mon, 24 Apr 2017 19:08:18 +0800

From: GitLab <my....@mycompany.com>

Reply-To: GitLab <my....@mycompany.com>

To: marsl...@mycompany.com

Message-ID: <58fddca2a24f6_3f0...@Gitlab.mail>

Subject: test subject

Mime-Version: 1.0

Content-Type: text/html;

charset=UTF-8

Content-Transfer-Encoding: 7bit

Auto-Submitted: auto-generated

X-Auto-Response-Suppress: All

<!DOCTYPE html PUBLIC "-//W3C//DTD HTML 4.0 Transitional//EN" "http://www.w3.org/TR/REC-html40/loose.dtd">

<html><body><p>test body</p></body></html>

OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:587:in `connect'

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:587:in `tlsconnect'

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:555:in `do_start'

from /opt/gitlab/embedded/lib/ruby/2.3.0/net/smtp.rb:521:in `start'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/mail-2.6.4/lib/mail/network/delivery_methods/smtp.rb:113:in `deliver!'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/mail-2.6.4/lib/mail/message.rb:2149:in `do_delivery'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/mail-2.6.4/lib/mail/message.rb:237:in `block in deliver'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/actionmailer-4.2.8/lib/action_mailer/base.rb:543:in `block in deliver_mail'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/activesupport-4.2.8/lib/active_support/notifications.rb:164:in `block in instrument'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/activesupport-4.2.8/lib/active_support/notifications/instrumenter.rb:20:in `instrument'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/activesupport-4.2.8/lib/active_support/notifications.rb:164:in `instrument'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/actionmailer-4.2.8/lib/action_mailer/base.rb:541:in `deliver_mail'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/mail-2.6.4/lib/mail/message.rb:237:in `deliver'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/actionmailer-4.2.8/lib/action_mailer/message_delivery.rb:85:in `deliver_now'

from (irb):1

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/railties-4.2.8/lib/rails/commands/console.rb:110:in `start'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/railties-4.2.8/lib/rails/commands/console.rb:9:in `start'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/railties-4.2.8/lib/rails/commands/commands_tasks.rb:68:in `console'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/railties-4.2.8/lib/rails/commands/commands_tasks.rb:39:in `run_command!'

from /opt/gitlab/embedded/lib/ruby/gems/2.3.0/gems/railties-4.2.8/lib/rails/commands.rb:17:in `<top (required)>'

from bin/rails:9:in `require'

from bin/rails:9:in `<main>'

Postfix Configuration:

# postconf -n

alias_database = hash:/etc/aliases

alias_maps = hash:/etc/aliases

append_dot_mydomain = no

biff = no

broken_sasl_auth_clients = yes

inet_interfaces = all

inet_protocols = all

mailbox_size_limit = 0

mydestination = $myhostname, Gitlab, www.gitlab.mycompany.com CNHSZHDCS1VU107, localhost.localdomain, localhost

myhostname = www.gitlab.mycompany.com

mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128

readme_directory = no

recipient_delimiter = +

relayhost =

smtp_sasl_auth_enable = yes

smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu)

smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination

smtpd_sasl_auth_enable = yes

smtpd_sasl_security_options = noplaintext

smtpd_tls_auth_only = yes

smtpd_tls_cert_file = /etc/ssl/certs/ssl-cert-snakeoil.pem

smtpd_tls_key_file = /etc/ssl/private/ssl-cert-snakeoil.key

smtpd_tls_security_level = may

smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache

smtpd_use_tls = yes

# postconf -M

smtp inet n - y - - smtpd

pickup unix n - y 60 1 pickup

cleanup unix n - y - 0 cleanup

qmgr unix n - n 300 1 qmgr

tlsmgr unix - - y 1000? 1 tlsmgr

rewrite unix - - y - - trivial-rewrite

bounce unix - - y - 0 bounce

defer unix - - y - 0 bounce

trace unix - - y - 0 bounce

verify unix - - y - 1 verify

flush unix n - y 1000? 0 flush

proxymap unix - - n - - proxymap

proxywrite unix - - n - 1 proxymap

smtp unix - - y - - smtp

relay unix - - y - - smtp

showq unix n - y - - showq

error unix - - y - - error

retry unix - - y - - error

discard unix - - y - - discard

local unix - n n - - local

virtual unix - n n - - virtual

lmtp unix - - y - - lmtp

anvil unix - - y - 1 anvil

scache unix - - y - 1 scache

maildrop unix - n n - - pipe flags=DRhu user=vmail argv=/usr/bin/maildrop -d ${recipient}

uucp unix - n n - - pipe flags=Fqhu user=uucp argv=uux -r -n -z -a$sender - $nexthop!rmail ($recipient)

ifmail unix - n n - - pipe flags=F user=ftn argv=/usr/lib/ifmail/ifmail -r $nexthop ($recipient)

bsmtp unix - n n - - pipe flags=Fq. user=bsmtp argv=/usr/lib/bsmtp/bsmtp -t$nexthop -f$sender $recipient

scalemail-backend unix - n n - 2 pipe flags=R user=scalemail argv=/usr/lib/scalemail/bin/scalemail-store ${nexthop} ${user} ${extension}

mailman unix - n n - - pipe flags=FR user=list argv=/usr/lib/mailman/bin/postfix-to-mailman.py ${nexthop} ${user}

Aleksey Tsalolikhin

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Apr 24, 2017, 8:17:14 AM4/24/17

to gitl...@googlegroups.com

What does the mail server log say?

On Apr 24, 2017 8:03 AM, "Marslo Jiao" <marsl...@gmail.com> wrote:

After the gitlab_rails['smtp_tls'] = false set to gitlab_rails['smtp_tls'] = true

The error shows to OPENSSL error, but still haven't any clue about it.

irb(main):001:0> Notify.test_email('marslo.ji...@mycompany.com', 'test subject', 'test body').deliver_now

Notify#test_email: processed outbound mail in 408.9ms

Sent mail to marsl...@mycompany.com (545.2ms)
Date: Mon, 24 Apr 2017 19:08:18 +0800
From: GitLab <my....@mycompany.com>
Reply-To: GitLab <my....@mycompany.com>
To: marsl...@mycompany.com

Message-ID: <58fddca2a24f6_3f0c3fd89a4db11c643c0@Gitlab.mail>

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