4 files changed, 29 insertions, 4 deletions
diff --git a/actionmailer/CHANGELOG b/actionmailer/CHANGELOG
index d8636fd83d..4ae7b91327 100644
--- a/actionmailer/CHANGELOG
+++ b/actionmailer/CHANGELOG
@@ -1,3 +1,8 @@
+*2.2.1 [RC2 or 2.2 final]*
+
+* Turn on STARTTLS if it is available in Net::SMTP (added in Ruby 1.8.7) and the SMTP server supports it (This is required for Gmail's SMTP server) #1336 [Grant Hollingworth]
+
+
 *2.2.0 [RC1] (October 24th, 2008)*
 
 * Add layout functionality to mailers [Pratik]
diff --git a/actionmailer/lib/action_mailer/base.rb b/actionmailer/lib/action_mailer/base.rb
index 043f56ba17..d63a608109 100644
--- a/actionmailer/lib/action_mailer/base.rb
+++ b/actionmailer/lib/action_mailer/base.rb
@@ -663,8 +663,10 @@ module ActionMailer #:nodoc:
         mail.ready_to_send
         sender = mail['return-path'] || mail.from
 
-        Net::SMTP.start(smtp_settings[:address], smtp_settings[:port], smtp_settings[:domain],
-            smtp_settings[:user_name], smtp_settings[:password], smtp_settings[:authentication]) do |smtp|
+        smtp = Net::SMTP.new(smtp_settings[:address], smtp_settings[:port])
+        smtp.enable_starttls_auto if smtp.respond_to?(:enable_starttls_auto)
+        smtp.start(smtp_settings[:domain], smtp_settings[:user_name], smtp_settings[:password],
+                   smtp_settings[:authentication]) do |smtp|
           smtp.sendmail(mail.encoded, sender, destinations)
         end
       end
diff --git a/actionmailer/test/abstract_unit.rb b/actionmailer/test/abstract_unit.rb
index 905f25c9f7..1617b88c8e 100644
--- a/actionmailer/test/abstract_unit.rb
+++ b/actionmailer/test/abstract_unit.rb
@@ -24,11 +24,15 @@ class MockSMTP
   def sendmail(mail, from, to)
     @@deliveries << [mail, from, to]
   end
+
+  def start(*args)
+    yield self
+  end
 end
 
 class Net::SMTP
-  def self.start(*args)
-    yield MockSMTP.new
+  def self.new(*args)
+    MockSMTP.new
   end
 end
 
diff --git a/actionmailer/test/mail_service_test.rb b/actionmailer/test/mail_service_test.rb
index 7f9540c44b..f5cb372b2a 100644
--- a/actionmailer/test/mail_service_test.rb
+++ b/actionmailer/test/mail_service_test.rb
@@ -938,6 +938,20 @@ EOF
     mail = TestMailer.create_body_ivar(@recipient)
     assert_equal "body: foo\nbar: baz", mail.body
   end
+
+  def test_starttls_is_enabled_if_supported
+    MockSMTP.any_instance.expects(:respond_to?).with(:enable_starttls_auto).returns(true)
+    MockSMTP.any_instance.expects(:enable_starttls_auto)
+    ActionMailer::Base.delivery_method = :smtp
+    TestMailer.deliver_signed_up(@recipient)
+  end
+
+  def test_starttls_is_disabled_if_not_supported
+    MockSMTP.any_instance.expects(:respond_to?).with(:enable_starttls_auto).returns(false)
+    MockSMTP.any_instance.expects(:enable_starttls_auto).never
+    ActionMailer::Base.delivery_method = :smtp
+    TestMailer.deliver_signed_up(@recipient)
+  end
 end
 
 end # uses_mocha