Redmine

I can't do much without additional information since I can't reproduce this problem.
To turn email debugging on, comment out this line in config/environments/production.rb:

config.action_mailer.logger = nil

then restart the app and create a new ticket.
Please tell me if you see a raw email dump in your log file.

You can also comment out this line:

config.action_mailer.raise_delivery_errors = false

so that an exception is raised if the email delivery fails.

I think there might be a problem with my ROR installation. I just wonder, why it works for sending news notifications. The output after enabling the logging and delivery error raising I get the following:

Net::SMTPFatalError (550 5.7.1 Unable to relay
):
    /usr/lib/ruby/1.8/net/smtp.rb:930:in `check_response'
    /usr/lib/ruby/1.8/net/smtp.rb:899:in `getok'
    /usr/lib/ruby/1.8/net/smtp.rb:842:in `rcptto'
    /usr/lib/ruby/1.8/net/smtp.rb:834:in `rcptto_list'
    /usr/lib/ruby/1.8/net/smtp.rb:833:in `each'
    /usr/lib/ruby/1.8/net/smtp.rb:833:in `rcptto_list'
    /usr/lib/ruby/1.8/net/smtp.rb:654:in `sendmail'
    /var/lib/gems/1.8/gems/actionmailer-2.1.0/lib/action_mailer/base.rb:629:in `perform_delivery_smtp'
    /usr/lib/ruby/1.8/net/smtp.rb:526:in `start'
    /usr/lib/ruby/1.8/net/smtp.rb:463:in `start'
    /var/lib/gems/1.8/gems/actionmailer-2.1.0/lib/action_mailer/base.rb:627:in `perform_delivery_smtp'
    /var/lib/gems/1.8/gems/actionmailer-2.1.0/lib/action_mailer/base.rb:508:in `__send__'
    /var/lib/gems/1.8/gems/actionmailer-2.1.0/lib/action_mailer/base.rb:508:in `deliver!'
    /app/models/mailer.rb:154:in `deliver!'
    /var/lib/gems/1.8/gems/actionmailer-2.1.0/lib/action_mailer/base.rb:383:in `method_missing'
    /app/controllers/issues_controller.rb:145:in `new'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/base.rb:1162:in `send'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/base.rb:1162:in `perform_action_without_filters'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/filters.rb:580:in `call_filters'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/filters.rb:573:in `perform_action_without_benchmark'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/benchmarking.rb:68:in `perform_action_without_rescue'
    /usr/lib/ruby/1.8/benchmark.rb:293:in `measure'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/benchmarking.rb:68:in `perform_action_without_rescue'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/rescue.rb:201:in `perform_action_without_caching'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/caching/sql_cache.rb:13:in `perform_action'
    /var/lib/gems/1.8/gems/activerecord-2.1.0/lib/active_record/connection_adapters/abstract/query_cache.rb:33:in `cache'
    /var/lib/gems/1.8/gems/activerecord-2.1.0/lib/active_record/query_cache.rb:8:in `cache'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/caching/sql_cache.rb:12:in `perform_action'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/base.rb:529:in `send'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/base.rb:529:in `process_without_filters'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/filters.rb:569:in `process_without_session_management_support'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/session_management.rb:130:in `process'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/base.rb:389:in `process'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/dispatcher.rb:149:in `handle_request'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/dispatcher.rb:107:in `dispatch'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/dispatcher.rb:104:in `synchronize'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/dispatcher.rb:104:in `dispatch'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/dispatcher.rb:120:in `dispatch_cgi'
    /var/lib/gems/1.8/gems/actionpack-2.1.0/lib/action_controller/dispatcher.rb:35:in `dispatch'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel/rails.rb:76:in `process'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel/rails.rb:74:in `synchronize'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel/rails.rb:74:in `process'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:159:in `process_client'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:158:in `each'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:158:in `process_client'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:285:in `run'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:285:in `initialize'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:285:in `new'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:285:in `run'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:268:in `initialize'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:268:in `new'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel.rb:268:in `run'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel/configurator.rb:282:in `run'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel/configurator.rb:281:in `each'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel/configurator.rb:281:in `run'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/mongrel_rails:128:in `run'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/../lib/mongrel/command.rb:212:in `run'
    /var/lib/gems/1.8/gems/mongrel-1.1.5/bin/mongrel_rails:281
    /var/lib/gems/1.8/bin/mongrel_rails:19:in `load'
    /var/lib/gems/1.8/bin/mongrel_rails:19

Looking at the code I think it might be a problem with getting the recipients.

Is there an easy way to dump what Redmine is trying to do? I would like to see, to whom exactly Redmine is trying to send mail to.

I think it is here:

Net::SMTPFatalError (550 5.7.1 Unable to relay):

You are trying to send your emails through an SMTP server that is set to block mail relaying or otherwise not configured as you need. Probably an email configuration issue rather than a redmine problem?

Well, that's the strange about it: it does work notification of new news.

What is the difference in sending a new news notification and a ticket information? I don't even see an event in the mail server logs (Exchange 2007R2) for those mails, that don't get sent.

BTW I forgot to mention that it did work with earlier Redmine versions (unfortunately I can't tell you, when it broke for me). And I didn't change any email configuration after this.