I'm trying to configure SMTP in a fresh Redmine installation, and currently email deliveries fail due to wrong configuration.

But the mere fact of inability to send emails renders the system unusable - no issue can be updated - any modification causes an internal error.

This is a bug - email delivery should be separated from the ticket update process (protected with a kind of try/catch if we're talking in Java/C++ terms).

The error page:

Internal error

An error occurred on the page you were trying to access.
If you continue to experience problems please contact your redMine administrator for assistance.

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The problem with SMTP (from production.log):

Processing IssuesController#edit (for 84.94.77.194 at 2010-06-17 06:56:38) [POST]
  Parameters: {"time_entry"=>{"comments"=>"", "activity_id"=>"", "hours"=>""}, "commit"=>"Submit", "action"=>"edit", "authenticity_token"=>"6Hg80reGYr7v47adr
GBjER4O0m8khpI/vOpdVsHekHI=", "id"=>"342", "notes"=>"sadfasdasd", "controller"=>"issues", "issue"=>{"start_date"=>"2010-06-17", "estimated_hours"=>"", "lock_
version"=>"0", "priority_id"=>"4", "subject"=>"email test", "fixed_version_id"=>"", "category_id"=>"", "description"=>"email test", "tracker_id"=>"3", "done_
ratio"=>"0", "due_date"=>"", "assigned_to_id"=>"6", "custom_field_values"=>{"5"=>""}}, "attachments"=>{"1"=>{"description"=>""}}}

Net::SMTPSyntaxError (501 Syntax: HELO hostname
):
  /usr/lib/ruby/1.8/net/smtp.rb:680:in `check_response'
  /usr/lib/ruby/1.8/net/smtp.rb:653:in `getok'
  /usr/lib/ruby/1.8/net/smtp.rb:623:in `helo'
  /usr/lib/ruby/1.8/net/smtp.rb:401:in `do_start'
  /usr/lib/ruby/1.8/net/smtp.rb:378:in `start'
  app/models/mailer.rb:287:in `deliver!'
  app/models/journal_observer.rb:20:in `after_create'
  /usr/lib/ruby/1.8/observer.rb:185:in `notify_observers'
  /usr/lib/ruby/1.8/observer.rb:184:in `each'
  /usr/lib/ruby/1.8/observer.rb:184:in `notify_observers'
  app/models/journal.rb:43:in `save'
  app/models/issue.rb:459:in `create_journal'
  app/controllers/issues_controller.rb:196:in `edit'
  passenger (2.2.11) lib/phusion_passenger/rack/request_handler.rb:92:in `process_request'
  passenger (2.2.11) lib/phusion_passenger/abstract_request_handler.rb:207:in `main_loop'
  passenger (2.2.11) lib/phusion_passenger/railz/application_spawner.rb:418:in `start_request_handler'
  passenger (2.2.11) lib/phusion_passenger/railz/application_spawner.rb:358:in `handle_spawn_application'
  passenger (2.2.11) lib/phusion_passenger/utils.rb:184:in `safe_fork'
  passenger (2.2.11) lib/phusion_passenger/railz/application_spawner.rb:354:in `handle_spawn_application'
  passenger (2.2.11) lib/phusion_passenger/abstract_server.rb:352:in `__send__'
  passenger (2.2.11) lib/phusion_passenger/abstract_server.rb:352:in `main_loop'
  passenger (2.2.11) lib/phusion_passenger/abstract_server.rb:196:in `start_synchronously'
  passenger (2.2.11) lib/phusion_passenger/abstract_server.rb:163:in `start'
  passenger (2.2.11) lib/phusion_passenger/railz/application_spawner.rb:213:in `start'
  passenger (2.2.11) lib/phusion_passenger/spawn_manager.rb:262:in `spawn_rails_application'
  passenger (2.2.11) lib/phusion_passenger/abstract_server_collection.rb:126:in `lookup_or_add'
  passenger (2.2.11) lib/phusion_passenger/spawn_manager.rb:256:in `spawn_rails_application'
  passenger (2.2.11) lib/phusion_passenger/abstract_server_collection.rb:80:in `synchronize'
  passenger (2.2.11) lib/phusion_passenger/abstract_server_collection.rb:79:in `synchronize'
  passenger (2.2.11) lib/phusion_passenger/spawn_manager.rb:255:in `spawn_rails_application'
  passenger (2.2.11) lib/phusion_passenger/spawn_manager.rb:154:in `spawn_application'