title: Debugging an SMTP Timeout Error
body: <p>I'm working on a Rails project that utilizes Action Mailer to send out mail campaigns. For the moment I have been testing everything with a plain old GMail account. Getting closer to release now and I've decided to switch the smtp server to our local mail server.</p>
  
  <p>This is all well and dandy until we attempt to actually send mail. With these new smtp server settings the mailer does nothing but time out:</p>
  
  <pre><code>MY_SMTP_SETTINGS = {
    :address =&gt; 'oz.some.server.edu',
    :port =&gt; 465,
    :user_name =&gt; MY_USERNAME,
    :authentication =&gt; :login,
    :password =&gt; MY_PASSWORD
  }
  </code></pre>
  
  <p>This is the stack trace from the error I receive some time after trying to send a campaign:</p>
  
  <pre><code>    Timeout::Error: execution expired
      from /opt/local/lib/ruby/1.8/timeout.rb:60:in `rbuf_fill'
      from /opt/local/lib/ruby/1.8/net/protocol.rb:134:in `rbuf_fill'
      from /opt/local/lib/ruby/1.8/net/protocol.rb:116:in `readuntil'
      from /opt/local/lib/ruby/1.8/net/protocol.rb:126:in `readline'
      from /opt/local/lib/ruby/1.8/net/smtp.rb:911:in `recv_response'
      from /opt/local/lib/ruby/gems/1.8/gems/ambethia-smtp-tls-1.1.2/lib/smtp-tls.rb:19:in `do_start'
      from /opt/local/lib/ruby/1.8/net/smtp.rb:921:in `critical'
      from /opt/local/lib/ruby/gems/1.8/gems/ambethia-smtp-tls-1.1.2/lib/smtp-tls.rb:19:in `do_start'
      from /opt/local/lib/ruby/1.8/net/smtp.rb:525:in `start'
      from /opt/local/lib/ruby/gems/1.8/gems/actionmailer-2.3.2/lib/action_mailer/base.rb:681:in `perform_delivery_smtp'
      from /opt/local/lib/ruby/gems/1.8/gems/actionmailer-2.3.2/lib/action_mailer/base.rb:523:in `__send__'
      from /opt/local/lib/ruby/gems/1.8/gems/actionmailer-2.3.2/lib/action_mailer/base.rb:523:in `deliver!'
      from /opt/local/lib/ruby/gems/1.8/gems/actionmailer-2.3.2/lib/action_mailer/base.rb:395:in `method_missing'
      from /Users/ryan/Development/gsoc/cohort/repo/app/models/freemailer_campaign.rb:39:in `send_campaign'
      from /opt/local/lib/ruby/gems/1.8/gems/activerecord-2.3.2/lib/active_record/associations/association_collection.rb:364:in `method_missing_without_paginate'
      from /opt/local/lib/ruby/gems/1.8/gems/activerecord-2.3.2/lib/active_record/associations/association_proxy.rb:219:in `method_missing'
      from /opt/local/lib/ruby/gems/1.8/gems/activerecord-2.3.2/lib/active_record/associations/association_proxy.rb:219:in `each'
      from /opt/local/lib/ruby/gems/1.8/gems/activerecord-2.3.2/lib/active_record/associations/association_proxy.rb:219:in `send'
      from /opt/local/lib/ruby/gems/1.8/gems/activerecord-2.3.2/lib/active_record/associations/association_proxy.rb:219:in `method_missing'
      from /opt/local/lib/ruby/gems/1.8/gems/activerecord-2.3.2/lib/active_record/associations/association_collection.rb:364:in `method_missing_without_paginate'
      from /Users/ryan/Development/gsoc/cohort/repo/vendor/plugins/will_paginate/lib/will_paginate/finder.rb:167:in `method_missing'
      from /Users/ryan/Development/gsoc/cohort/repo/app/models/freemailer_campaign.rb:37:in `send_campaign'
  </code></pre>
  
  <p>Do anyone have any idea how I can pinpoint my problem?</p>