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.j...@mycompany.com', 'test 
subject', 'test body').deliver_now*

*Notify#test_email: processed outbound mail in 408.9ms*

*Sent mail to marslo.j...@mycompany.com (545.2ms)*
*Date: Mon, 24 Apr 2017 19:08:18 +0800*
*From: GitLab <my.m...@mycompany.com>*
*Reply-To: GitLab <my.m...@mycompany.com>*
*To: marslo.j...@mycompany.com*
*Message-ID: <58fddca2a24f6_3f0c3fd89a4db11c64...@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}*


On Thursday, March 16, 2017 at 5:03:35 PM UTC+8, Magnus Therning wrote:
>
>
> Marslo Jiao <marsl...@gmail.com <javascript:>> 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 <javascript:> 
> 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 
>

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