Error while sending email through Gmail.
Added by David Díaz over 12 years ago
I get the error: "Ha ocurrido un error mientras enviando el correo (SSL_connect returned=1 errno=0 state=unknown state: unknown protocol)"
System configuration:
- Ubuntu 64
- Apache 2.2
- mod_passenger
Environment configuration:
Environment:
- Redmine version 2.0.0.stable.9699
- Ruby version 1.9.3 (x86_64-linux)
- Rails version 3.2.3
- Environment production
- Database adapter PostgreSQL
Redmine plugins:
no plugin installed
I'm using Redmine 2.0 stable after upgrading from 1.3 (where this configuration works) with the following gemset:
actionmailer (3.2.3)
actionpack (3.2.3)
activemodel (3.2.3)
activerecord (3.2.3)
activeresource (3.2.3)
activesupport (3.2.3)
arel (3.0.2)
builder (3.0.0)
bundler (1.1.3)
coderay (1.0.6)
daemon_controller (1.0.0)
erubis (2.7.0)
fastthread (1.0.7)
hike (1.2.1)
i18n (0.6.0)
journey (1.0.3)
json (1.7.3)
mail (2.4.4)
mime-types (1.18)
multi_json (1.3.5)
net-ldap (0.3.1)
passenger (3.0.12)
pg (0.13.2)
polyglot (0.3.3)
prototype-rails (3.2.1)
rack (1.4.1)
rack-cache (1.2)
rack-openid (1.3.1)
rack-ssl (1.3.2)
rack-test (0.6.1)
rails (3.2.3)
railties (3.2.3)
rake (0.9.2.2)
rdoc (3.12)
rmagick (2.13.1)
ruby-openid (2.1.8)
rubygems-bundler (1.0.0)
rvm (1.11.3.3)
sprockets (2.1.3)
sqlite3 (1.3.6)
thor (0.14.6)
tilt (1.3.3)
treetop (1.4.10)
tzinfo (0.3.33)
My email configuration is:
production: email_delivery: delivery_method: :smtp smtp_settings: tls: true enable_starttls_auto: true address: "smtp.gmail.com" port: '587' domain: "smtp.gmail.com" authentication: :plain user_name: "<user@gmail.com>" password: "<password>"
Thanks
Replies (35)
RE: Error while sending email through Gmail.
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Added by Aleksander Demidov over 12 years ago
Yes. I connect in this topic. Redmine 2.0 + Rails 3 = not work sending email via gmail.
action_mailer_optional_tls plugin not work.
Unable to setting SSL an this doc: http://edgeguides.rubyonrails.org/action_mailer_basics.html#action-mailer-configuration-for-gmail
Any ideas?
SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol
RE: Error while sending email through Gmail.
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Added by David Díaz over 12 years ago
Hi! I found that it is a configuration problem.
First, use the configuration.yml of the redmine2.0 instalation. Don't copy/paste from another version. Then, check all the document to comment all the email configuration blocks. Then use the following email configuration block with exactly the same quotes (only on user_name):
production: email_delivery: delivery_method: :smtp smtp_settings: enable_starttls_auto: true address: smtp.gmail.com port: 587 domain: smtp.gmail.com authentication: :plain user_name: "user@gmail.com" password: password
RE: Error while sending email through Gmail.
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Added by Aleksander Demidov over 12 years ago
David Díaz wrote:
ohh.. no. It is not work. Without option "tls: true" - I fetched error "530 5.7.0 Must issue a STARTTLS command first". It`s one.Hi! I found that it is a configuration problem.
First, use the configuration.yml of the redmine2.0 instalation. Don't copy/paste from another version. Then, check all the document to comment all the email configuration blocks. Then use the following email configuration block with exactly the same quotes (only on user_name):
[...]
It`s two: Quotes allowed for password and user_name fields - this doc http://www.redmine.org/projects/redmine/wiki/EmailConfiguration#Asynchronous-delivery_methods
OR
in source configuration.yml.example https://github.com/redmine/redmine/blob/master/config/configuration.yml.example
@# ==== SMTP server at using TLS (GMail) #
- This might require some additional configuration. See the guides at:
- http://www.redmine.org/projects/redmine/wiki/EmailConfiguration #
- production:
- email_delivery:
- delivery_method: :smtp
- smtp_settings:
- tls: true
- enable_starttls_auto: true
- address: "smtp.gmail.com"
- port: 587
- domain: "smtp.gmail.com" # 'your.domain.com' for GoogleApps
- authentication: :plain
- user_name: "your_email@gmail.com"
- password: "your_password"@
After execute test email notification - fetched error "SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol".
David, maybe you install in your machine special tls plugin. How did you that?
RE: Error while sending email through Gmail.
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Added by unisol solo over 12 years ago
"SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol".
help!
RE: Error while sending email through Gmail.
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Added by unisol solo over 12 years ago
delivery_method: :smtp
smtp_settings:
address: smtp.gmail.com
port: 587
domain: substancelab.com
authentication: login
user_name: "foobar@example.net"
password: passw0rd
enable_starttls_auto: true
WORK!!!
delete - tls: true
RE: Error while sending email through Gmail.
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Added by David Díaz over 12 years ago
Hi, Aleksander Demidov.
Remove tls: true. You only need enable_starttls_auto: true to enable tls. And then remove quotes (", ") on address, domain and password. The gems that i've installed are posted above and i don't have any special tls gem.
Hope this help you.
RE: Error while sending email through Gmail.
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Added by Aleksander Demidov over 12 years ago
Maybe, I use old version gem`s. But gemfile in redmine-2.0 write new version of my gems.
Gem list:
abstract (1.0.0) action_mailer_tls (1.1.3) actionmailer (3.2.3, 3.1.0, 3.0.0, 2.3.14, 2.3.11, 2.3.5) actionpack (3.2.3, 3.1.0, 3.0.0, 2.3.14, 2.3.11, 2.3.5) activemodel (3.2.3, 3.1.0, 3.0.0) activerecord (3.2.3, 3.1.0, 3.0.0, 2.3.14, 2.3.11, 2.3.5) activeresource (3.2.3, 3.1.0, 3.0.0, 2.3.14, 2.3.11, 2.3.5) activesupport (3.2.3, 3.1.0, 3.0.0, 2.3.14, 2.3.11, 2.3.5) ambethia-smtp-tls (1.1.2) arel (3.0.2, 2.2.1, 1.0.1) bcrypt-ruby (3.0.1) builder (3.0.0, 2.1.2) bundler (1.1.3, 1.0.18) capistrano (2.12.0) cgi_multipart_eof_fix (2.5.0) coderay (1.0.6) daemon_controller (0.2.6) daemons (1.1.8, 1.0.10) dispatcher (0.0.1) erubis (2.7.0, 2.6.6) eventmachine (0.12.10) fastercsv (1.5.5) fastthread (1.0.7) gem_plugin (0.2.3) highline (1.6.12) hike (1.2.1) i18n (0.6.0, 0.4.2) journey (1.0.3) jruby-pageant (1.0.2) json (1.7.3) mail (2.4.4, 2.3.0, 2.2.19) mime-types (1.18, 1.16) mongrel (1.2.0.pre2, 1.1.5) mongrel_cluster (1.0.5) multi_json (1.3.5, 1.0.3) mysql (2.8.1) net-ldap (0.3.1) net-scp (1.0.4) net-sftp (2.0.5) net-ssh (2.4.0) net-ssh-gateway (1.1.0) passenger (3.0.9) pg (0.13.2) polyglot (0.3.3, 0.3.2) prototype-rails (3.2.1) rack (1.4.1, 1.1.0) rack-cache (1.2, 1.0.3) rack-mount (0.8.3, 0.6.14) rack-openid (1.3.1) rack-ssl (1.3.2) rack-test (0.6.1, 0.5.7) rails (3.2.3, 3.1.0, 3.0.0, 2.3.14, 2.3.11) railties (3.2.3, 3.1.0, 3.0.0) rake (0.9.2.2, 0.9.2) rdoc (3.12, 3.9.4, 2.4.2) rmagick (2.13.1) ruby-openid (2.1.8) rubygems-update (1.8.24) rubytree (0.8.2) sprockets (2.1.3, 2.0.0) sqlite3 (1.3.6) thin (1.3.1) thor (0.14.6) tilt (1.3.3) treetop (1.4.10) tzinfo (0.3.33, 0.3.29)
My gemfile.lock (in redmine-2.0 directory):
GEM remote: http://rubygems.org/ specs: actionmailer (3.2.3) actionpack (= 3.2.3) mail (~> 2.4.4) actionpack (3.2.3) activemodel (= 3.2.3) activesupport (= 3.2.3) builder (~> 3.0.0) erubis (~> 2.7.0) journey (~> 1.0.1) rack (~> 1.4.0) rack-cache (~> 1.2) rack-test (~> 0.6.1) sprockets (~> 2.1.2) activemodel (3.2.3) activesupport (= 3.2.3) builder (~> 3.0.0) activerecord (3.2.3) activemodel (= 3.2.3) activesupport (= 3.2.3) arel (~> 3.0.2) tzinfo (~> 0.3.29) activeresource (3.2.3) activemodel (= 3.2.3) activesupport (= 3.2.3) activesupport (3.2.3) i18n (~> 0.6) multi_json (~> 1.0) arel (3.0.2) builder (3.0.0) cgi_multipart_eof_fix (2.5.0) coderay (1.0.6) daemons (1.1.8) dispatcher (0.0.1) erubis (2.7.0) fastercsv (1.5.5) fastthread (1.0.7) gem_plugin (0.2.3) hike (1.2.1) i18n (0.6.0) journey (1.0.3) json (1.7.3) mail (2.4.4) i18n (>= 0.4.0) mime-types (~> 1.16) treetop (~> 1.4.8) metaclass (0.0.1) mime-types (1.18) mocha (0.11.4) metaclass (~> 0.0.1) mongrel (1.2.0.pre2) daemons (~> 1.0.10) gem_plugin (~> 0.2.3) multi_json (1.3.5) mysql (2.8.1) mysql2 (0.3.11) net-ldap (0.3.1) pg (0.13.2) polyglot (0.3.3) prototype-rails (3.2.1) rails (~> 3.2) rack (1.4.1) rack-cache (1.2) rack (>= 0.4) rack-openid (1.3.1) rack (>= 1.1.0) ruby-openid (>= 2.1.8) rack-ssl (1.3.2) rack rack-test (0.6.1) rack (>= 1.0) rails (3.2.3) actionmailer (= 3.2.3) actionpack (= 3.2.3) activerecord (= 3.2.3) activeresource (= 3.2.3) activesupport (= 3.2.3) bundler (~> 1.0) railties (= 3.2.3) railties (3.2.3) actionpack (= 3.2.3) activesupport (= 3.2.3) rack-ssl (~> 1.3.2) rake (>= 0.8.7) rdoc (~> 3.4) thor (~> 0.14.6) rake (0.9.2.2) rdoc (3.12) json (~> 1.4) rmagick (2.13.1) ruby-openid (2.1.8) shoulda (2.11.3) sprockets (2.1.3) hike (~> 1.2) rack (~> 1.0) tilt (~> 1.1, != 1.3.0) sqlite3 (1.3.6) thor (0.14.6) tilt (1.3.3) treetop (1.4.10) polyglot polyglot (>= 0.3.1) tzinfo (0.3.33) PLATFORMS ruby DEPENDENCIES activerecord-jdbcmysql-adapter activerecord-jdbcpostgresql-adapter activerecord-jdbcsqlite3-adapter builder cgi_multipart_eof_fix coderay (~> 1.0.6) dispatcher fastercsv (~> 1.5.0) fastthread i18n (~> 0.6.0) jruby-openssl mocha mongrel (= 1.2.0.pre2) mysql mysql2 (~> 0.3.11) net-ldap (~> 0.3.1) pg (>= 0.11.0) prototype-rails (= 3.2.1) rack-openid rails (= 3.2.3) rdoc (>= 2.4.2) rmagick (>= 2.0.0) ruby-openid (~> 2.1.4) shoulda (~> 2.11) sqlite3
My settings in configuration.yml:
production: delivery_method: :smtp smtp_settings: address: smtp.gmail.com port: 587 domain: smtp.gmail.com authentication: :login user_name: "myusername@gmail.com" password: mypassword enable_starttls_auto: true
After execute test notification mail, fetch error: "530 5.7.0 Must issue a STARTTLS command first. n19sm30590948bkv.14".
Why in you it work, but from my not work?
RE: Error while sending email through Gmail.
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Added by Sungjin Kim about 12 years ago
I have solved in Redmine 2.0
1. Don't install "action_mailer_optional_tls" plugin.
2. Copy gmail setting example in "configuration.example" into "configuration.xml"
IMPORTANT : Keep space and tab .
# production: # email_delivery: # delivery_method: :smtp # smtp_settings: # tls: true # enable_starttls_auto: true # address: "smtp.gmail.com" # port: 587 # domain: "smtp.gmail.com" # 'your.domain.com' for GoogleApps # authentication: :plain # user_name: "your_email@gmail.com" # password: "your_password"
3. Remove "#" and # 'your.domain.com' for GoogleApps and "tls:true" and quotes in address and domain and password. Only remain quotes in user_name.
IMPORTANT : Keep space and tab .
production: email_delivery: delivery_method: :smtp smtp_settings: enable_starttls_auto: true address: "smtp.gmail.com" port: 587 domain: "smtp.gmail.com" authentication: :plain user_name: "your_email@gmail.com" password: "your_password"
4. Set your Gmail setting
IMPORTANT : Keep space and tab .
production: email_delivery: delivery_method: :smtp smtp_settings: enable_starttls_auto: true address: smtp.gmail.com port: 587 domain: smtp.gmail.com authentication: :plain user_name: "kskyj_test@gmail.com" password: 123455
5. Have fun :0
RE: Error while sending email through Gmail.
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Added by Plam Sim over 10 years ago
It works perfect for Redmine 2.4.1 and Gmail SMTP method. I used the syntax described by Sungjin Kim. Thank you very much.
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
I know that is a old problem but in redmine 3.0.3 i got whe following error:
(Permission denied - connect(2) for "smtp.bsservices.com.br" port 587)
Im using:
Environment:
Redmine version 3.0.3.stable
Ruby version 2.2.2-p95 (2015-04-13) [x86_64-linux]
Rails version 4.2.1
Environment production
Database adapter Mysql2
SCM:
Filesystem
Redmine plugins:
no plugin installed
configuration.yml:
default:
# Outgoing emails configuration (see examples above)
email_delivery:
delivery_method: :smtp
smtp_settings:
address: "smtp.bsservices.com.br"
port: 587
domain: "smtp.bsservices.com.br"
authentication: :login
user_name: '<user>@bsservices.com.br'
password: '<password>'
openssl_verify_mode: 'none'
RE: Error while sending email through Gmail.
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Added by Plam Sim over 7 years ago
Hello,
please try with these settings and be very careful to copy paste it exactly like the example below - be careful for "" or non ""
production: email_delivery: delivery_method: :smtp smtp_settings: enable_starttls_auto: true address: "smtp.bsservices.com.br" port: 587 domain: smtp.bsservices.com.br authentication: :plain user_name: "your-user@your-domain.com" password: ***********
Thiago Oliveira wrote:
I know that is a old problem but in redmine 3.0.3 i got whe following error:
(Permission denied - connect(2) for "smtp.bsservices.com.br" port 587)
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
Plam Sim. Thanks for the tips.
I did exactly what you asked for and the error persist. Maybe the bug is in some ruby configuration or permission to SELinux. I'm using CentOS 7.
RE: Error while sending email through Gmail.
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Added by Plam Sim over 7 years ago
I guess you see this "permission denied" message with trying to send a test email under Administration -> Settings -> Email notifications and then close to the bottom right "Send a test email"? Or you see it from another place?
Thiago Oliveira wrote:
I did exactly what you asked for and the error persist. Maybe the bug is in some ruby configuration or permission to SELinux. I'm using CentOS 7.
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
Actually yes. But I also see this error in the log when a task is created and the notification email is not sent.
RE: Error while sending email through Gmail.
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Added by Plam Sim over 7 years ago
My suggestion is to create a new Gmail account, activate POP / SMTP for this Gmail and try with my suggestion for the configuration.yml syntax. In that way you can be sure that the issue is not with the syntax.
Thiago Oliveira wrote:
Actually yes. But I also see this error in the log when a task is created and the notification email is not sent.
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
Pam. I tried using gmail and the error is the same. I made a java class to send email and the email is sent normally. Do you know if there is any specific ruby lib or redmine to send email?
RE: Error while sending email through Gmail.
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Added by Plam Sim over 7 years ago
Hi, yest they are. I use also Centos 7.x . But my Ruby is 3.0. I can send emails with no problem.
My gems form mail are versions:
# gem list | grep mail actionmailer (5.0.0.1, 4.2.7.1) mail (2.6.4)
Thiago Oliveira wrote:
Pam. I tried using gmail and the error is the same. I made a java class to send email and the email is sent normally. Do you know if there is any specific ruby lib or redmine to send email?
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
This is what I have:
# gem list | grep mail
actionmailer (4.2.7.1, 4.2.1, 3.2.6)
mail (2.6.4, 2.5.3, 2.4.4)
Maybe if update the ruby and the gem. What you think?
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
Look into apache logs i found this:App 5821 stderr: /bin/bash: /home/www-data/.bash_profile: Permission denied
App 5821 stdout:
App 5821 stderr: /usr/local/lib/ruby/gems/2.2.0/gems/htmlentities-4.3.1/lib/htmlentities/mappings/expanded.rb:465: warning: duplicated key at line 466 ignored: "inodot"
App 5821 stderr: Rails Error: Unable to access log file. Please ensure that /var/www/redmine/log/production.log exists and is writable (ie, make it writable for user and group: chmod 0664 /var/www/redmine/log/production.log). The log level has been raised to WARN and the output directed to STDERR until the problem is fixed.
Any help?
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
In upload files there is an error for permission denied as well. Maybe they are connected.
I already gave all permission to the folder (777):
App 6529 stderr: Saving attachment '/var/www/redmine/files/2016/12/161223114939_app_creator.PNG' (79469 bytes)
rb_sysopen - /var/www/redmine/files/2016/12/161223114939_app_creator.PNG):
App 6529 stderr: Completed 500 Internal Server Error in 18ms (ActiveRecord: 2.5ms)
App 6529 stderr:
App 6529 stderr: Errno::EACCES (Permission denied
App 6529 stderr: app/models/attachment.rb:109:in `initialize'
App 6529 stderr: app/models/attachment.rb:109:in `open'
App 6529 stderr: app/models/attachment.rb:109:in `files_to_final_location'
App 6529 stderr: app/controllers/attachments_controller.rb:90:in `upload'
@
RE: Error while sending email through Gmail.
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Added by Plam Sim over 7 years ago
I think your redmine installation has to be checked. You should use separate user to own the Redmine folder. You should invoke bundler commands from this user.
Let's say you create new user and group for Redmine
### Create Redmine user and group redus:redus ### Redmine folder has to be owned by these user and group sudo chown -R redus:redus /usr/local/share/redmine ### Give permissions in visudo redus ALL=(ALL) NOPASSWD: /usr/local/share/redmine/bin/rake redus ALL=(ALL) NOPASSWD: /usr/local/share/redmine/bin/Rakefile ### Repeat bundler install through the new user redus su - redus cd /usr/local/share/redmine/ bundle install --without development test postgresql sqlite bundle exec rake generate_secret_token bundle exec rake db:migrate RAILS_ENV=production ### Restart httpd or nginx service service httpd restart (or service nginx restart)
This should solve your permissions issues.
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
Pam. Thanks for the tips.
I made it, but not working and executing this steps I got it:
bundle exec rake generate_secret_token
/usr/local/lib/ruby/gems/2.2.0/gems/htmlentities-4.3.1/lib/htmlentities/mappings/expanded.rb:465: warning: duplicated key at line 466 ignored: "inodot"
bundle exec rake db:migrate RAILS_ENV=production
/usr/local/lib/ruby/gems/2.2.0/gems/htmlentities-4.3.1/lib/htmlentities/mappings/expanded.rb:465: warning: duplicated key at line 466 ignored: "inodot"
I dont know what I missing. Maybe its a silly step.
RE: Error while sending email through Gmail.
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Added by Plam Sim over 7 years ago
You mentioned above that you use Redmine 3.0.3. I am not sure if Ruby 2.2 supports Redmine 3.0.x. Redmine 3.0.x is not mentioned here:
http://www.redmine.org/projects/redmine/wiki/RedmineInstall#Requirements
My suggestion is to update Redmine to latest 3.3.1. You can do it and then repeat the commands I suggested above. Redmine 3.3.1 should work with Ruby 2.2.
RE: Error while sending email through Gmail.
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Added by Plam Sim over 7 years ago
You may try with this:
http://stackoverflow.com/questions/27669855/warnings-after-upgrading-to-ruby-2-2-0
Update htmentities or open the file and remove the duplicate key
vi /usr/local/lib/ruby/gems/2.2.0/gems/htmlentities-4.3.1/lib/htmlentities/mappings/expanded.r
:465 (go to line 465)
Thiago Oliveira wrote:
bundle exec rake generate_secret_token
/usr/local/lib/ruby/gems/2.2.0/gems/htmlentities-4.3.1/lib/htmlentities/mappings/expanded.rb:465: warning: duplicated key at line 466 ignored: "inodot"
RE: Error while sending email through Gmail.
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Added by Thiago Oliveira over 7 years ago
Pam... I will install the 3.3 version. But i cant do it right now.
I will do it later and I post the results here.
Thanks again for patience and the tips.