Why are my Authentication Emails not working? I get an "AuthenticationError"

Whenever I reset my password or attempt to get an email confirmation I see this sort of error page: `Net::SMTPAuthenticationError in Devise::PasswordsController#create` It looks like the email is sending as I see this in my Rails Server logs, however at the bottom of it you can see I get some sort of 500 error. This only happens when I'm sending email authentication from development (I've included my development.rb file below). Seems to be working fine on Heroku. I've included my email logins on a separate .env file so you don't see it here and I've changed my email address in these logs for privacy. Any help is appreciated! Rails Server Logs: ``` (0.9ms) commit transaction Rendered devise/mailer/confirmation_instructions.html.erb (1.1ms) Sent mail to xx@xx.com (958.0ms) Date: Wed, 23 Apr 2014 10:51:46 -0700 From: xx@xx.com Reply-To: xx@xx.com To: xx@xx.com Message-ID: <5357fdb28f720_199810d2ab033cb@unknown20c9d07bac9b.mail> Subject: Confirmation instructions Mime-Version: 1.0 Content-Type: text/html; charset=UTF-8 Content-Transfer-Encoding: 7bit <p>Welcome xx@xx.com!</p> <p>You can confirm your account email through the link below:</p> <p><a href="http://localhost:3000/users/confirmation?confirmation_token=ukG1PXbXyXP5LpjG1Eaa">Confirm my account</a></p> Completed 500 Internal Server Error in 964ms Net::SMTPAuthenticationError (530-5.5.1 Authentication Required. Learn more at ): /usr/local/rvm/rubies/ruby-1.9.3-p392/lib/ruby/1.9.1/net/smtp.rb:948:in `check_response' /usr/local/rvm/rubies/ruby-1.9.3-p392/lib/ruby/1.9.1/net/smtp.rb:917:in `getok' /usr/local/rvm/rubies/ruby-1.9.3-p392/lib/ruby/1.9.1/net/smtp.rb:832:in `mailfrom' /usr/local/rvm/rubies/ruby-1.9.3-p392/lib/ruby/1.9.1/net/smtp.rb:659:in `send_message' mail (2.5.4) lib/mail/network/delivery_methods/smtp.rb:113:in `block in deliver!' /usr/local/rvm/rubies/ruby-1.9.3-p392/lib/ruby/1.9.1/net/smtp.rb:520:in `start' mail (2.5.4) lib/mail/network/delivery_methods/smtp.rb:112:in `deliver!' mail (2.5.4) lib/mail/message.rb:2129:in `do_delivery' mail (2.5.4) lib/mail/message.rb:232:in `block in deliver' actionmailer (4.0.0) lib/action_mailer/base.rb:456:in `block in deliver_mail' activesupport (4.0.0) lib/active_support/notifications.rb:159:in `block in instrument' activesupport (4.0.0) lib/active_support/notifications/instrumenter.rb:20:in `instrument' activesupport (4.0.0) lib/active_support/notifications.rb:159:in `instrument' actionmailer (4.0.0) lib/action_mailer/base.rb:454:in `deliver_mail' mail (2.5.4) lib/mail/message.rb:232:in `deliver' devise (3.2.4) lib/devise/models/authenticatable.rb:173:in `send_devise_notification' devise (3.2.4) lib/devise/models/confirmable.rb:102:in `send_confirmation_instructions' devise (3.2.4) lib/devise/models/confirmable.rb:117:in `block in resend_confirmation_instructions' devise (3.2.4) lib/devise/models/confirmable.rb:211:in `pending_any_confirmation' devise (3.2.4) lib/devise/models/confirmable.rb:116:in `resend_confirmation_instructions' devise (3.2.4) lib/devise/models/confirmable.rb:265:in `send_confirmation_instructions' devise (3.2.4) app/controllers/devise/confirmations_controller.rb:9:in `create' actionpack (4.0.0) lib/action_controller/metal/implicit_render.rb:4:in `send_action' actionpack (4.0.0) lib/abstract_controller/base.rb:189:in `process_action' actionpack (4.0.0) lib/action_controller/metal/rendering.rb:10:in `process_action' actionpack (4.0.0) lib/abstract_controller/callbacks.rb:18:in `block in process_action' activesupport (4.0.0) lib/active_support/callbacks.rb:423:in `_run__3176473197347058618__process_action__callbacks' activesupport (4.0.0) lib/active_support/callbacks.rb:80:in `run_callbacks' actionpack (4.0.0) lib/abstract_controller/callbacks.rb:17:in `process_action' actionpack (4.0.0) lib/action_controller/metal/rescue.rb:29:in `process_action' actionpack (4.0.0) lib/action_controller/metal/instrumentation.rb:31:in `block in process_action' activesupport (4.0.0) lib/active_support/notifications.rb:159:in `block in instrument' activesupport (4.0.0) lib/active_support/notifications/instrumenter.rb:20:in `instrument' activesupport (4.0.0) lib/active_support/notifications.rb:159:in `instrument' actionpack (4.0.0) lib/action_controller/metal/instrumentation.rb:30:in `process_action' actionpack (4.0.0) 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lib/action_dispatch/journey/router.rb:59:in `call' actionpack (4.0.0) lib/action_dispatch/routing/route_set.rb:655:in `call' warden (1.2.3) lib/warden/manager.rb:35:in `block in call' warden (1.2.3) lib/warden/manager.rb:34:in `catch' warden (1.2.3) lib/warden/manager.rb:34:in `call' rack (1.5.2) lib/rack/etag.rb:23:in `call' rack (1.5.2) lib/rack/conditionalget.rb:35:in `call' rack (1.5.2) lib/rack/head.rb:11:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/params_parser.rb:27:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/flash.rb:241:in `call' rack (1.5.2) lib/rack/session/abstract/id.rb:225:in `context' rack (1.5.2) lib/rack/session/abstract/id.rb:220:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/cookies.rb:486:in `call' activerecord (4.0.0) lib/active_record/query_cache.rb:36:in `call' activerecord (4.0.0) lib/active_record/connection_adapters/abstract/connection_pool.rb:626:in `call' activerecord (4.0.0) lib/active_record/migration.rb:369:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/callbacks.rb:29:in `block in call' activesupport (4.0.0) lib/active_support/callbacks.rb:373:in `_run__455108311755261639__call__callbacks' activesupport (4.0.0) lib/active_support/callbacks.rb:80:in `run_callbacks' actionpack (4.0.0) lib/action_dispatch/middleware/callbacks.rb:27:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/reloader.rb:64:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/remote_ip.rb:76:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/debug_exceptions.rb:17:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/show_exceptions.rb:30:in `call' railties (4.0.0) lib/rails/rack/logger.rb:38:in `call_app' railties (4.0.0) lib/rails/rack/logger.rb:21:in `block in call' activesupport (4.0.0) lib/active_support/tagged_logging.rb:67:in `block in tagged' activesupport (4.0.0) lib/active_support/tagged_logging.rb:25:in `tagged' activesupport (4.0.0) lib/active_support/tagged_logging.rb:67:in `tagged' railties (4.0.0) lib/rails/rack/logger.rb:21:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/request_id.rb:21:in `call' rack (1.5.2) lib/rack/methodoverride.rb:21:in `call' rack (1.5.2) lib/rack/runtime.rb:17:in `call' activesupport (4.0.0) lib/active_support/cache/strategy/local_cache.rb:83:in `call' rack (1.5.2) lib/rack/lock.rb:17:in `call' actionpack (4.0.0) lib/action_dispatch/middleware/static.rb:64:in `call' railties (4.0.0) lib/rails/engine.rb:511:in `call' railties (4.0.0) lib/rails/application.rb:97:in `call' rack (1.5.2) lib/rack/lock.rb:17:in `call' rack (1.5.2) lib/rack/content_length.rb:14:in `call' rack (1.5.2) lib/rack/handler/webrick.rb:60:in `service' /usr/local/rvm/rubies/ruby-1.9.3-p392/lib/ruby/1.9.1/webrick/httpserver.rb:138:in `service' /usr/local/rvm/rubies/ruby-1.9.3-p392/lib/ruby/1.9.1/webrick/httpserver.rb:94:in `run' /usr/local/rvm/rubies/ruby-1.9.3-p392/lib/ruby/1.9.1/webrick/server.rb:191:in `block in start_thread' Rendered /usr/local/rvm/gems/ruby-1.9.3-p392/gems/actionpack-4.0.0/lib/action_dispatch/middleware/templates/rescues/_source.erb (0.9ms) Rendered /usr/local/rvm/gems/ruby-1.9.3-p392/gems/actionpack-4.0.0/lib/action_dispatch/middleware/templates/rescues/_trace.erb (1.1ms) Rendered /usr/local/rvm/gems/ruby-1.9.3-p392/gems/actionpack-4.0.0/lib/action_dispatch/middleware/templates/rescues/_request_and_response.erb (0.9ms) Rendered /usr/local/rvm/gems/ruby-1.9.3-p392/gems/actionpack-4.0.0/lib/action_dispatch/middleware/templates/rescues/diagnostics.erb within rescues/layout (16.0ms) ``` development.rb : ``` Yoshirt::Application.configure do # Settings specified here will take precedence over those in config/application.rb. # In the development environment your application's code is reloaded on # every request. This slows down response time but is perfect for development # since you don't have to restart the web server when you make code changes. config.cache_classes = false # Do not eager load code on boot. config.eager_load = false # Show full error reports and disable caching. config.consider_all_requests_local = true config.action_controller.perform_caching = false # Don't care if the mailer can't send. config.action_mailer.raise_delivery_errors = false # Print deprecation notices to the Rails logger. config.active_support.deprecation = :log # Raise an error on page load if there are pending migrations config.active_record.migration_error = :page_load # Debug mode disables concatenation and preprocessing of assets. # This option may cause significant delays in view rendering with a large # number of complex assets. config.assets.debug = true # Defining default url options for devise config.action_mailer.default_url_options = { host: 'localhost', port: 3000 } # Change to true to allow email to be sent during development # http://stackoverflow.com/questions/21610815/how-to-config-devise-gem-to-send-email-to-the-resource config.action_mailer.perform_deliveries = true config.action_mailer.raise_delivery_errors = true config.action_mailer.delivery_method = :smtp config.action_mailer.smtp_settings = { address: "smtp.gmail.com", port: 587, domain: "mail.google.com",####important authentication: "plain", enable_starttls_auto: true, user_name: ENV["GMAIL_USERNAME"], password: ENV["GMAIL_PASSWORD"] } end ```