Failed to send email with configurations for smtp.office365.com
Follow the official instructions to install gitlab with docker. It works well with older versions.
But it will be failed to deliver an email with below errors once upgraded to GitLab Community Edition 8.16.4 f32ee822. Is there any root certificate missing from this release for smtp.office365.com:587?
2017-02-07_04:27:39.88046 2017-02-07T04:27:39.880Z 1512 TID-ox1ohvufk ActionMailer::DeliveryJob JID-b6ab3f9e12fe8c5d0c95635d INFO: Adding dead ActiveJob::QueueAdapters::SidekiqAdapter::JobWrapper job b6ab3f9e12fe8c5d0c95635d
2017-02-07_04:27:39.88156 2017-02-07T04:27:39.881Z 1512 TID-ox1ohvufk ActionMailer::DeliveryJob JID-b6ab3f9e12fe8c5d0c95635d INFO: fail: 0.11 sec
2017-02-07_04:27:39.88187 2017-02-07T04:27:39.881Z 1512 TID-ox1ohvufk WARN: {"context":"Job raised exception","job":{"class":"ActiveJob::QueueAdapters::SidekiqAdapter::JobWrapper","wrapped":"ActionMailer::DeliveryJob","queue":"mailers","args":[{"job_class":"ActionMailer::DeliveryJob","job_id":"ee77fc2d-82ee-409c-b120-639d6b2cbfee","queue_name":"mailers","arguments":["Notify","new_ssh_key_email","deliver_now",30],"locale":"en"}],"retry":3,"jid":"b6ab3f9e12fe8c5d0c95635d","created_at":1486441481.7166846,"enqueued_at":1486441659.768735,"error_message":"SSL_connect returned=1 errno=0 state=error: certificate verify failed","error_class":"OpenSSL::SSL::SSLError","failed_at":1486441482.026953,"retry_count":3,"retried_at":1486441659.8801973},"jobstr":"{\"class\":\"ActiveJob::QueueAdapters::SidekiqAdapter::JobWrapper\",\"wrapped\":\"ActionMailer::DeliveryJob\",\"queue\":\"mailers\",\"args\":[{\"job_class\":\"ActionMailer::DeliveryJob\",\"job_id\":\"ee77fc2d-82ee-409c-b120-639d6b2cbfee\",\"queue_name\":\"mailers\",\"arguments\":[\"Notify\",\"new_ssh_key_email\",\"deliver_now\",30],\"locale\":\"en\"}],\"retry\":3,\"jid\":\"b6ab3f9e12fe8c5d0c95635d\",\"created_at\":1486441481.7166846,\"enqueued_at\":1486441659.768735,\"error_message\":\"SSL_connect returned=1 errno=0 state=error: certificate verify failed\",\"error_class\":\"OpenSSL::SSL::SSLError\",\"failed_at\":1486441482.026953,\"retry_count\":2,\"retried_at\":1486441594.778514}"}
2017-02-07_04:27:39.88207 2017-02-07T04:27:39.881Z 1512 TID-ox1ohvufk WARN: OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=error: certificate verify failed
2017-02-07_04:27:39.88230 2017-02-07T04:27:39.882Z 1512 TID-ox1ohvufk WARN: /opt/gitlab/embedded/lib/ruby/2.3.0/net/http.rb:933:in `connect_nonblock'
2017-02-07_04:27:39.88232 /opt/gitlab/embedded/lib/ruby/2.3.0/net/http.rb:933:in `connect'
2017-02-07_04:27:39.88234 /opt/gitlab/embedded/lib/ruby/2.3.0/net/http.rb:863:in `do_start'
2017-02-07_04:27:39.88235 /opt/gitlab/embedded/lib/ruby/2.3.0/net/http.rb:852:in `start'
2017-02-07_04:27:39.88236 /opt/gitlab/embedded/lib/ruby/2.3.0/net/http.rb:584:in `start'
2017-02-07_04:27:39.88236 /opt/gitlab/embedded/lib/ruby/2.3.0/net/http.rb:479:in `get_response'
2017-02-07_04:27:39.88237 /opt/gitlab/embedded/lib/ruby/2.3.0/net/http.rb:456:in `get'
Below is the configuration used:
gitlab_rails['smtp_enable'] = true
gitlab_rails['smtp_address'] = "smtp.office365.com"
gitlab_rails['smtp_port'] = 587
gitlab_rails['smtp_user_name'] = "myusername@company.com"
gitlab_rails['smtp_password'] = "mypassword"
gitlab_rails['smtp_domain'] = "smtp.office365.com"
gitlab_rails['smtp_authentication'] = "login"
gitlab_rails['smtp_enable_starttls_auto'] = true
gitlab_rails['smtp_openssl_verify_mode'] = 'none'
gitlab_rails['smtp_tls'] = false
gitlab_rails['gitlab_email_display_name'] = 'My Gitlab Server'
gitlab_rails['gitlab_email_from'] = 'gitlab@company.com'
gitlab_rails['gitlab_email_reply_to'] = 'noreply@company.com'
I have also tried with the gitlab-rails console as below, it can send email successful.
Notify.test_email('myusername@company.com', 'Message Subject test', 'Message Body test').deliver_now