From 4875bc2ba1670289a34a155569af2f51abddc316 Mon Sep 17 00:00:00 2001
From: Jeremy Kemper <jeremy@bitsweat.net>
Date: Mon, 10 Dec 2012 23:04:19 -0700
Subject: [PATCH] Expose the SMTP envelope From and To addresses and allow them
 to be overridden.

Envelope From address defaults to return_path || sender || from_addrs.first.
Envelope To address defaults to destinations (to + cc + bcc).

Updates all delivery methods to rely on the SMTP envelope.

References #421 and rails/rails#5985
---
 lib/mail/check_delivery_params.rb             | 16 ++--
 lib/mail/message.rb                           | 79 ++++++++++++++++
 lib/mail/network/delivery_methods/sendmail.rb | 18 ++--
 lib/mail/network/delivery_methods/smtp.rb     | 10 +--
 .../delivery_methods/smtp_connection.rb       | 12 +--
 spec/mail/message_spec.rb                     | 62 +++++++++++++
 .../network/delivery_methods/exim_spec.rb     | 24 ++---
 .../delivery_methods/file_delivery_spec.rb    |  4 +-
 .../network/delivery_methods/sendmail_spec.rb | 89 ++++++++++---------
 .../delivery_methods/smtp_connection_spec.rb  | 11 ++-
 .../network/delivery_methods/smtp_spec.rb     | 51 ++++-------
 .../delivery_methods/test_mailer_spec.rb      |  4 +-
 12 files changed, 252 insertions(+), 128 deletions(-)

diff --git a/lib/mail/check_delivery_params.rb b/lib/mail/check_delivery_params.rb
index 0a287ca78..669ad4656 100644
--- a/lib/mail/check_delivery_params.rb
+++ b/lib/mail/check_delivery_params.rb
@@ -1,22 +1,20 @@
 module Mail
   module CheckDeliveryParams
     def check_delivery_params(mail)
-      envelope_from = mail.return_path || mail.sender || mail.from_addrs.first
-      if envelope_from.blank?
-        raise ArgumentError.new('A sender (Return-Path, Sender or From) required to send a message')
+      if mail.smtp_envelope_from.blank?
+        raise ArgumentError.new('An SMTP From address is required to send a message. Set the message smtp_envelope_from, return_path, sender, or from address.')
       end
 
-      destinations ||= mail.destinations if mail.respond_to?(:destinations) && mail.destinations
-      if destinations.blank?
-        raise ArgumentError.new('At least one recipient (To, Cc or Bcc) is required to send a message')
+      if mail.smtp_envelope_to.blank?
+        raise ArgumentError.new('An SMTP To address is required to send a message. Set the message smtp_envelope_to, to, cc, or bcc address.')
       end
 
-      message ||= mail.encoded if mail.respond_to?(:encoded)
+      message = mail.encoded if mail.respond_to?(:encoded)
       if message.blank?
-        raise ArgumentError.new('A encoded content is required to send a message')
+        raise ArgumentError.new('An encoded message is required to send an email')
       end
 
-      [envelope_from, destinations, message]
+      [mail.smtp_envelope_from, mail.smtp_envelope_to, message]
     end
   end
 end
diff --git a/lib/mail/message.rb b/lib/mail/message.rb
index 6d1298297..d98eaec7d 100644
--- a/lib/mail/message.rb
+++ b/lib/mail/message.rb
@@ -108,6 +108,9 @@ def initialize(*args, &block)
       @charset = 'UTF-8'
       @defaulted_charset = true
 
+      @smtp_envelope_from = nil
+      @smtp_envelope_to = nil
+
       @perform_deliveries = true
       @raise_delivery_errors = true
 
@@ -1023,6 +1026,82 @@ def sender=( val )
       header[:sender] = val
     end
 
+    # Returns the SMTP Envelope From value of the mail object, as a single
+    # string of an address spec.
+    #
+    # Defaults to Return-Path, Sender, or the first From address.
+    #
+    # Example:
+    #
+    #  mail.smtp_envelope_from = 'Mikel <mikel@test.lindsaar.net>'
+    #  mail.smtp_envelope_from #=> 'mikel@test.lindsaar.net'
+    #
+    # Also allows you to set the value by passing a value as a parameter
+    #
+    # Example:
+    #
+    #  mail.smtp_envelope_from 'Mikel <mikel@test.lindsaar.net>'
+    #  mail.smtp_envelope_from #=> 'mikel@test.lindsaar.net'
+    def smtp_envelope_from( val = nil )
+      if val
+        self.smtp_envelope_from = val
+      else
+        @smtp_envelope_from || return_path || sender || from_addrs.first
+      end
+    end
+
+    # Sets the From address on the SMTP Envelope.
+    #
+    # Example:
+    #
+    #  mail.smtp_envelope_from = 'Mikel <mikel@test.lindsaar.net>'
+    #  mail.smtp_envelope_from #=> 'mikel@test.lindsaar.net'
+    def smtp_envelope_from=( val )
+      @smtp_envelope_from = val
+    end
+
+    # Returns the SMTP Envelope To value of the mail object.
+    #
+    # Defaults to #destinations: To, Cc, and Bcc addresses.
+    #
+    # Example:
+    #
+    #  mail.smtp_envelope_to = 'Mikel <mikel@test.lindsaar.net>'
+    #  mail.smtp_envelope_to #=> 'mikel@test.lindsaar.net'
+    #
+    # Also allows you to set the value by passing a value as a parameter
+    #
+    # Example:
+    #
+    #  mail.smtp_envelope_to ['Mikel <mikel@test.lindsaar.net>', 'Lindsaar <lindsaar@test.lindsaar.net>']
+    #  mail.smtp_envelope_to #=> ['mikel@test.lindsaar.net', 'lindsaar@test.lindsaar.net']
+    def smtp_envelope_to( val = nil )
+      if val
+        self.smtp_envelope_to = val
+      else
+        @smtp_envelope_to || destinations
+      end
+    end
+
+    # Sets the To addresses on the SMTP Envelope.
+    #
+    # Example:
+    #
+    #  mail.smtp_envelope_to = 'Mikel <mikel@test.lindsaar.net>'
+    #  mail.smtp_envelope_to #=> 'mikel@test.lindsaar.net'
+    #
+    #  mail.smtp_envelope_to = ['Mikel <mikel@test.lindsaar.net>', 'Lindsaar <lindsaar@test.lindsaar.net>']
+    #  mail.smtp_envelope_to #=> ['mikel@test.lindsaar.net', 'lindsaar@test.lindsaar.net']
+    def smtp_envelope_to=( val )
+      @smtp_envelope_to =
+        case val
+        when Array, NilClass
+          val
+        else
+          [val]
+        end
+    end
+
     # Returns the decoded value of the subject field, as a single string.
     #
     # Example:
diff --git a/lib/mail/network/delivery_methods/sendmail.rb b/lib/mail/network/delivery_methods/sendmail.rb
index e87e66fa0..1491d0390 100644
--- a/lib/mail/network/delivery_methods/sendmail.rb
+++ b/lib/mail/network/delivery_methods/sendmail.rb
@@ -41,26 +41,24 @@ class Sendmail
 
     def initialize(values)
       self.settings = { :location       => '/usr/sbin/sendmail',
-                        :arguments      => '-i -t' }.merge(values)
+                        :arguments      => '-i' }.merge(values)
     end
 
     attr_accessor :settings
 
     def deliver!(mail)
-      check_delivery_params(mail)
+      smtp_from, smtp_to, message = check_delivery_params(mail)
 
-      envelope_from = mail.return_path || mail.sender || mail.from_addrs.first
-      return_path = "-f #{self.class.shellquote(envelope_from)}" if envelope_from
+      from = "-f #{self.class.shellquote(smtp_from)}"
+      to = smtp_to.map { |to| self.class.shellquote(to) }.join(' ')
 
-      arguments = [settings[:arguments], return_path, '--'].compact.join(" ")
-
-      quoted_destinations = mail.destinations.collect { |d| self.class.shellquote(d) }
-      self.class.call(settings[:location], arguments, quoted_destinations.join(' '), mail)
+      arguments = "#{settings[:arguments]} #{from} --"
+      self.class.call(settings[:location], arguments, to, message)
     end
 
-    def self.call(path, arguments, destinations, mail)
+    def self.call(path, arguments, destinations, encoded_message)
       popen "#{path} #{arguments} #{destinations}" do |io|
-        io.puts mail.encoded.to_lf
+        io.puts encoded_message.to_lf
         io.flush
       end
     end
diff --git a/lib/mail/network/delivery_methods/smtp.rb b/lib/mail/network/delivery_methods/smtp.rb
index a095385a0..6904ef38f 100644
--- a/lib/mail/network/delivery_methods/smtp.rb
+++ b/lib/mail/network/delivery_methods/smtp.rb
@@ -89,13 +89,13 @@ def initialize(values)
                         :tls                  => nil
                       }.merge!(values)
     end
-    
+
     attr_accessor :settings
-    
+
     # Send the message via SMTP.
     # The from and to attributes are optional. If not set, they are retrieve from the Message.
     def deliver!(mail)
-      envelope_from, destinations, message = check_delivery_params(mail)
+      smtp_from, smtp_to, message = check_delivery_params(mail)
 
       smtp = Net::SMTP.new(settings[:address], settings[:port])
       if settings[:tls] || settings[:ssl]
@@ -107,10 +107,10 @@ def deliver!(mail)
           smtp.enable_starttls_auto(ssl_context)
         end
       end
-      
+
       response = nil
       smtp.start(settings[:domain], settings[:user_name], settings[:password], settings[:authentication]) do |smtp_obj|
-        response = smtp_obj.sendmail(message, envelope_from, destinations)
+        response = smtp_obj.sendmail(message, smtp_from, smtp_to)
       end
 
       if settings[:return_response]
diff --git a/lib/mail/network/delivery_methods/smtp_connection.rb b/lib/mail/network/delivery_methods/smtp_connection.rb
index b17e5c695..147335d8d 100644
--- a/lib/mail/network/delivery_methods/smtp_connection.rb
+++ b/lib/mail/network/delivery_methods/smtp_connection.rb
@@ -44,18 +44,18 @@ def initialize(values)
       self.smtp = values[:connection]
       self.settings = values
     end
-    
+
     attr_accessor :smtp
     attr_accessor :settings
-    
+
     # Send the message via SMTP.
     # The from and to attributes are optional. If not set, they are retrieve from the Message.
     def deliver!(mail)
-      envelope_from, destinations, message = check_delivery_params(mail)
-      response = smtp.sendmail(message, envelope_from, destinations)
+      smtp_from, smtp_to, message = check_delivery_params(mail)
+      response = smtp.sendmail(message, smtp_from, smtp_to)
 
-      settings[:return_response] ? response : self 
+      settings[:return_response] ? response : self
     end
-        
+
   end
 end
diff --git a/spec/mail/message_spec.rb b/spec/mail/message_spec.rb
index f66cf5a08..2b9c6e673 100644
--- a/spec/mail/message_spec.rb
+++ b/spec/mail/message_spec.rb
@@ -1731,4 +1731,66 @@ def self.delivering_email(mail)
 
   end
 
+  describe 'SMTP envelope From' do
+    it 'should respond' do
+      Mail::Message.new.should respond_to(:smtp_envelope_from)
+    end
+
+    it 'should default to return_path, sender, or first from address' do
+      message = Mail::Message.new do
+        return_path 'return'
+        sender 'sender'
+        from 'from'
+      end
+      message.smtp_envelope_from.should eq 'return'
+
+      message.return_path = nil
+      message.smtp_envelope_from.should eq 'sender'
+
+      message.sender = nil
+      message.smtp_envelope_from.should eq 'from'
+    end
+
+    it 'can be overridden' do
+      message = Mail::Message.new { return_path 'return' }
+
+      message.smtp_envelope_from = 'envelope_from'
+      message.smtp_envelope_from.should eq 'envelope_from'
+
+      message.smtp_envelope_from = 'declared_from'
+      message.smtp_envelope_from.should eq 'declared_from'
+
+      message.smtp_envelope_from = nil
+      message.smtp_envelope_from.should eq 'return'
+    end
+  end
+
+  describe 'SMTP envelope To' do
+    it 'should respond' do
+      Mail::Message.new.should respond_to(:smtp_envelope_to)
+    end
+
+    it 'should default to destinations' do
+      message = Mail::Message.new do
+        to 'to'
+        cc 'cc'
+        bcc 'bcc'
+      end
+      message.smtp_envelope_to.should eq message.destinations
+    end
+
+    it 'can be overridden' do
+      message = Mail::Message.new { to 'to' }
+
+      message.smtp_envelope_to = 'envelope_to'
+      message.smtp_envelope_to.should eq %w(envelope_to)
+
+      message.smtp_envelope_to = 'declared_to'
+      message.smtp_envelope_to.should eq %w(declared_to)
+
+      message.smtp_envelope_to = nil
+      message.smtp_envelope_to.should eq %w(to)
+    end
+  end
+
 end
diff --git a/spec/mail/network/delivery_methods/exim_spec.rb b/spec/mail/network/delivery_methods/exim_spec.rb
index d91ef1751..3b08064c3 100644
--- a/spec/mail/network/delivery_methods/exim_spec.rb
+++ b/spec/mail/network/delivery_methods/exim_spec.rb
@@ -30,7 +30,7 @@
     Mail::Exim.should_receive(:call).with('/usr/sbin/exim', 
                                           '-i -t -f "roger@test.lindsaar.net" --', 
                                           '"marcel@test.lindsaar.net" "bob@test.lindsaar.net"', 
-                                          mail)
+                                          mail.encoded)
     mail.deliver!
   end
 
@@ -54,7 +54,7 @@
       Mail::Exim.should_receive(:call).with('/usr/sbin/exim',
                                                 '-i -t -f "return@test.lindsaar.net" --', 
                                                 '"to@test.lindsaar.net"', 
-                                                mail)
+                                                mail.encoded)
                                                 
       mail.deliver
 
@@ -77,7 +77,7 @@
       Mail::Exim.should_receive(:call).with('/usr/sbin/exim',
                                                 '-i -t -f "sender@test.lindsaar.net" --', 
                                                 '"to@test.lindsaar.net"', 
-                                                mail)
+                                                mail.encoded)
 
       mail.deliver
     end
@@ -98,7 +98,7 @@
       Mail::Exim.should_receive(:call).with('/usr/sbin/exim',
                                                 '-i -t -f "from@test.lindsaar.net" --', 
                                                 '"to@test.lindsaar.net"', 
-                                                mail)
+                                                mail.encoded)
       mail.deliver
     end
 
@@ -118,7 +118,7 @@
       Mail::Exim.should_receive(:call).with('/usr/sbin/exim',
                                                 '-i -t -f "\"from+suffix test\"@test.lindsaar.net" --',
                                                 '"to@test.lindsaar.net"',
-                                                mail)
+                                                mail.encoded)
       mail.deliver
     end
 
@@ -135,7 +135,7 @@
       Mail::Exim.should_receive(:call).with('/usr/sbin/exim',
                                                 '-i -t -f "from@test.lindsaar.net" --',
                                                 '"-hyphen@test.lindsaar.net"',
-                                                mail)
+                                                mail.encoded)
       mail.deliver
     end
   end
@@ -152,9 +152,9 @@
     end
     
     Mail::Exim.should_receive(:call).with('/usr/sbin/exim', 
-                                              '-f "from@test.lindsaar.net" --', 
+                                              ' -f "from@test.lindsaar.net" --',
                                               '"marcel@test.lindsaar.net" "bob@test.lindsaar.net"', 
-                                              mail)
+                                              mail.encoded)
     mail.deliver!
   end
 
@@ -170,9 +170,9 @@
     end
     
     Mail::Exim.should_receive(:call).with('/usr/sbin/exim', 
-                                              "-f \"\\\"foo\\\\\\\"\\;touch /tmp/PWNED\\;\\\\\\\"\\\"@blah.com\" --", 
+                                              " -f \"\\\"foo\\\\\\\"\\;touch /tmp/PWNED\\;\\\\\\\"\\\"@blah.com\" --",
                                               '"marcel@test.lindsaar.net"', 
-                                              mail)
+                                              mail.encoded)
     mail.deliver!
   end
 
@@ -186,7 +186,7 @@
         subject "Email with no sender"
         body "body"
       end
-    end.should raise_error('A sender (Return-Path, Sender or From) required to send a message')
+    end.should raise_error('An SMTP From address is required to send a message. Set the message smtp_envelope_from, return_path, sender, or from address.')
   end
 
   it "should raise an error if no recipient if defined" do
@@ -199,6 +199,6 @@
         subject "Email with no recipient"
         body "body"
       end
-    end.should raise_error('At least one recipient (To, Cc or Bcc) is required to send a message')
+    end.should raise_error('An SMTP To address is required to send a message. Set the message smtp_envelope_to, to, cc, or bcc address.')
   end
 end
diff --git a/spec/mail/network/delivery_methods/file_delivery_spec.rb b/spec/mail/network/delivery_methods/file_delivery_spec.rb
index 62b19da87..ed93162dd 100644
--- a/spec/mail/network/delivery_methods/file_delivery_spec.rb
+++ b/spec/mail/network/delivery_methods/file_delivery_spec.rb
@@ -100,7 +100,7 @@
           subject "Email with no sender"
           body "body"
         end
-      end.should raise_error('A sender (Return-Path, Sender or From) required to send a message')
+      end.should raise_error('An SMTP From address is required to send a message. Set the message smtp_envelope_from, return_path, sender, or from address.')
     end
 
     it "should raise an error if no recipient if defined" do
@@ -114,7 +114,7 @@
           subject "Email with no recipient"
           body "body"
         end
-      end.should raise_error('At least one recipient (To, Cc or Bcc) is required to send a message')
+      end.should raise_error('An SMTP To address is required to send a message. Set the message smtp_envelope_to, to, cc, or bcc address.')
     end
 
   end
diff --git a/spec/mail/network/delivery_methods/sendmail_spec.rb b/spec/mail/network/delivery_methods/sendmail_spec.rb
index 55b30198f..46cfec971 100644
--- a/spec/mail/network/delivery_methods/sendmail_spec.rb
+++ b/spec/mail/network/delivery_methods/sendmail_spec.rb
@@ -28,9 +28,9 @@
     end
     
     Mail::Sendmail.should_receive(:call).with('/usr/sbin/sendmail', 
-                                              '-i -t -f "roger@test.lindsaar.net" --',
+                                              '-i -f "roger@test.lindsaar.net" --',
                                               '"marcel@test.lindsaar.net" "bob@test.lindsaar.net"', 
-                                              mail)
+                                              mail.encoded)
     mail.deliver!
   end
 
@@ -45,14 +45,14 @@
       subject 'invalid RFC2822'
     end
 
-    Mail::Sendmail.should_receive(:popen).with('/usr/sbin/sendmail -i -t -f "roger@test.lindsaar.net" -- "marcel@test.lindsaar.net" "bob@test.lindsaar.net"')
+    Mail::Sendmail.should_receive(:popen).with('/usr/sbin/sendmail -i -f "roger@test.lindsaar.net" -- "marcel@test.lindsaar.net" "bob@test.lindsaar.net"')
 
     mail.deliver!
   end
 
-  describe "return path" do
+  describe 'SMTP From' do
 
-    it "should send an email with a return-path using sendmail" do
+    it 'should explicitly pass an envelope From address to sendmail' do
       Mail.defaults do
         delivery_method :sendmail
       end
@@ -60,45 +60,46 @@
       mail = Mail.new do
         to "to@test.lindsaar.net"
         from "from@test.lindsaar.net"
-        sender "sender@test.lindsaar.net"
-        subject "Can't set the return-path"
-        return_path "return@test.lindsaar.net"
+        subject 'Can\'t set the return-path'
         message_id "<1234@test.lindsaar.net>"
         body "body"
+
+        smtp_envelope_from 'smtp_from@test.lindsaar.net'
       end
-      
+
       Mail::Sendmail.should_receive(:call).with('/usr/sbin/sendmail',
-                                                '-i -t -f "return@test.lindsaar.net" --',
+                                                '-i -f "smtp_from@test.lindsaar.net" --',
                                                 '"to@test.lindsaar.net"', 
-                                                mail)
-                                                
+                                                mail.encoded)
+
       mail.deliver
 
     end
 
-    it "should use the sender address is no return path is specified" do
+    it "should escape the From address" do
       Mail.defaults do
         delivery_method :sendmail
       end
 
       mail = Mail.new do
-        to "to@test.lindsaar.net"
-        from "from@test.lindsaar.net"
-        sender "sender@test.lindsaar.net"
-        subject "Can't set the return-path"
-        message_id "<1234@test.lindsaar.net>"
-        body "body"
+        to 'to@test.lindsaar.net'
+        from '"from+suffix test"@test.lindsaar.net'
+        subject 'Can\'t set the return-path'
+        message_id '<1234@test.lindsaar.net>'
+        body 'body'
       end
 
       Mail::Sendmail.should_receive(:call).with('/usr/sbin/sendmail',
-                                                '-i -t -f "sender@test.lindsaar.net" --',
-                                                '"to@test.lindsaar.net"', 
-                                                mail)
-
+                                                '-i -f "\"from+suffix test\"@test.lindsaar.net" --',
+                                                '"to@test.lindsaar.net"',
+                                                mail.encoded)
       mail.deliver
     end
-    
-    it "should use the from address is no return path or sender are specified" do
+  end
+
+  describe 'SMTP To' do
+
+    it 'should explicitly pass envelope To addresses to sendmail' do
       Mail.defaults do
         delivery_method :sendmail
       end
@@ -106,35 +107,37 @@
       mail = Mail.new do
         to "to@test.lindsaar.net"
         from "from@test.lindsaar.net"
-        subject "Can't set the return-path"
+        subject 'Can\'t set the return-path'
         message_id "<1234@test.lindsaar.net>"
         body "body"
+
+        smtp_envelope_to 'smtp_to@test.lindsaar.net'
       end
 
       Mail::Sendmail.should_receive(:call).with('/usr/sbin/sendmail',
-                                                '-i -t -f "from@test.lindsaar.net" --',
-                                                '"to@test.lindsaar.net"', 
-                                                mail)
+                                                '-i -f "from@test.lindsaar.net" --',
+                                                '"smtp_to@test.lindsaar.net"',
+                                                mail.encoded)
       mail.deliver
     end
 
-    it "should escape the return path address" do
+    it "should escape the To address" do
       Mail.defaults do
         delivery_method :sendmail
       end
 
       mail = Mail.new do
-        to 'to@test.lindsaar.net'
-        from '"from+suffix test"@test.lindsaar.net'
+        to '"to+suffix test"@test.lindsaar.net'
+        from 'from@test.lindsaar.net'
         subject 'Can\'t set the return-path'
         message_id '<1234@test.lindsaar.net>'
         body 'body'
       end
 
       Mail::Sendmail.should_receive(:call).with('/usr/sbin/sendmail',
-                                                '-i -t -f "\"from+suffix test\"@test.lindsaar.net" --',
-                                                '"to@test.lindsaar.net"',
-                                                mail)
+                                                '-i -f "from@test.lindsaar.net" --',
+                                                '"\"to+suffix test\"@test.lindsaar.net"',
+                                                mail.encoded)
       mail.deliver
     end
 
@@ -149,9 +152,9 @@
       end
 
       Mail::Sendmail.should_receive(:call).with('/usr/sbin/sendmail',
-                                                '-i -t -f "from@test.lindsaar.net" --',
+                                                '-i -f "from@test.lindsaar.net" --',
                                                 '"-hyphen@test.lindsaar.net"',
-                                                mail)
+                                                mail.encoded)
       mail.deliver
     end
   end
@@ -168,9 +171,9 @@
     end
     
     Mail::Sendmail.should_receive(:call).with('/usr/sbin/sendmail', 
-                                              '-f "from@test.lindsaar.net" --',
+                                              ' -f "from@test.lindsaar.net" --',
                                               '"marcel@test.lindsaar.net" "bob@test.lindsaar.net"', 
-                                              mail)
+                                              mail.encoded)
     mail.deliver!
   end
 
@@ -186,9 +189,9 @@
     end
     
     Mail::Sendmail.should_receive(:call).with('/usr/sbin/sendmail', 
-                                              "-f \"\\\"foo\\\\\\\"\\;touch /tmp/PWNED\\;\\\\\\\"\\\"@blah.com\" --",
+                                              " -f \"\\\"foo\\\\\\\"\\;touch /tmp/PWNED\\;\\\\\\\"\\\"@blah.com\" --",
                                               %("\\\"foo\\\\\\\"\\;touch /tmp/PWNED\\;\\\\\\\"\\\"@blah.com"), 
-                                              mail)
+                                              mail.encoded)
     mail.deliver!
   end
 
@@ -202,7 +205,7 @@
         subject "Email with no sender"
         body "body"
       end
-    end.should raise_error('A sender (Return-Path, Sender or From) required to send a message')
+    end.should raise_error('An SMTP From address is required to send a message. Set the message smtp_envelope_from, return_path, sender, or from address.')
   end
 
   it "should raise an error if no recipient if defined" do
@@ -215,6 +218,6 @@
         subject "Email with no recipient"
         body "body"
       end
-    end.should raise_error('At least one recipient (To, Cc or Bcc) is required to send a message')
+    end.should raise_error('An SMTP To address is required to send a message. Set the message smtp_envelope_to, to, cc, or bcc address.')
   end
 end
diff --git a/spec/mail/network/delivery_methods/smtp_connection_spec.rb b/spec/mail/network/delivery_methods/smtp_connection_spec.rb
index b517831a7..84a245e10 100644
--- a/spec/mail/network/delivery_methods/smtp_connection_spec.rb
+++ b/spec/mail/network/delivery_methods/smtp_connection_spec.rb
@@ -19,11 +19,14 @@
       from    'roger@test.lindsaar.net'
       to      'marcel@test.lindsaar.net, bob@test.lindsaar.net'
       subject 'invalid RFC2822'
+
+      smtp_envelope_from 'smtp_from'
+      smtp_envelope_to 'smtp_to'
     end
 
     MockSMTP.deliveries[0][0].should eq mail.encoded
-    MockSMTP.deliveries[0][1].should eq mail.from[0]
-    MockSMTP.deliveries[0][2].should eq mail.destinations    
+    MockSMTP.deliveries[0][1].should eq 'smtp_from'
+    MockSMTP.deliveries[0][2].should eq %w(smtp_to)
   end
 
   it "should be able to return actual SMTP protocol response" do
@@ -56,7 +59,7 @@
         subject "Email with no sender"
         body "body"
       end
-    end.should raise_error('A sender (Return-Path, Sender or From) required to send a message')
+    end.should raise_error('An SMTP From address is required to send a message. Set the message smtp_envelope_from, return_path, sender, or from address.')
   end
 
   it "should raise an error if no recipient if defined" do
@@ -71,6 +74,6 @@
         subject "Email with no recipient"
         body "body"
       end
-    end.should raise_error('At least one recipient (To, Cc or Bcc) is required to send a message')
+    end.should raise_error('An SMTP To address is required to send a message. Set the message smtp_envelope_to, to, cc, or bcc address.')
   end
 end
diff --git a/spec/mail/network/delivery_methods/smtp_spec.rb b/spec/mail/network/delivery_methods/smtp_spec.rb
index 9e56191bd..307c32875 100644
--- a/spec/mail/network/delivery_methods/smtp_spec.rb
+++ b/spec/mail/network/delivery_methods/smtp_spec.rb
@@ -29,11 +29,14 @@
         from    'roger@moore.com'
         to      'marcel@amont.com'
         subject 'invalid RFC2822'
+
+        smtp_envelope_from 'smtp_from'
+        smtp_envelope_to 'smtp_to'
       end
 
       MockSMTP.deliveries[0][0].should eq mail.encoded
-      MockSMTP.deliveries[0][1].should eq mail.from[0]
-      MockSMTP.deliveries[0][2].should eq mail.destinations
+      MockSMTP.deliveries[0][1].should eq 'smtp_from'
+      MockSMTP.deliveries[0][2].should eq %w(smtp_to)
     end
 
     it "should be able to send itself" do
@@ -149,53 +152,31 @@ def redefine_verify_none(new_value)
       doing { mail.deliver! }.should_not raise_error(TypeError)
     end
   end
-  
-  describe "return path" do
 
-    it "should use the return path if specified" do
-      Mail.deliver do
-        to "to@someemail.com"
-        from "from@someemail.com"
-        sender "sender@test.lindsaar.net"
-        subject "Can't set the return-path"
-        return_path "bounce@someemail.com" 
-        message_id "<1234@someemail.com>"
-        body "body"
-      end
-      MockSMTP.deliveries[0][1].should eq "bounce@someemail.com"
-    end
+  describe "SMTP Envelope" do
 
-    it "should use the sender address is no return path is specified" do
+    it "uses the envelope From and To addresses" do
       Mail.deliver do
         to "to@someemail.com"
         from "from@someemail.com"
-        sender "sender@test.lindsaar.net"
-        subject "Can't set the return-path"
-        message_id "<1234@someemail.com>"
-        body "body"
-      end
-      MockSMTP.deliveries[0][1].should eq "sender@test.lindsaar.net"
-    end
-    
-    it "should use the from address is no return path or sender is specified" do
-      Mail.deliver do
-        to "to@someemail.com"
-        from "from@someemail.com"
-        subject "Can't set the return-path"
         message_id "<1234@someemail.com>"
         body "body"
+
+        smtp_envelope_to "smtp_to@someemail.com"
+        smtp_envelope_from "smtp_from@someemail.com"
       end
-      MockSMTP.deliveries[0][1].should eq "from@someemail.com"
+      MockSMTP.deliveries[0][1].should eq 'smtp_from@someemail.com'
+      MockSMTP.deliveries[0][2].should eq %w(smtp_to@someemail.com)
     end
 
-    it "should raise an error if no sender is defined" do
+    it "should raise if there is no envelope From address" do
       lambda do
         Mail.deliver do
           to "to@somemail.com"
           subject "Email with no sender"
           body "body"
         end
-      end.should raise_error('A sender (Return-Path, Sender or From) required to send a message')
+      end.should raise_error('An SMTP From address is required to send a message. Set the message smtp_envelope_from, return_path, sender, or from address.')
     end
 
     it "should raise an error if no recipient if defined" do
@@ -205,8 +186,8 @@ def redefine_verify_none(new_value)
           subject "Email with no recipient"
           body "body"
         end
-      end.should raise_error('At least one recipient (To, Cc or Bcc) is required to send a message')
+      end.should raise_error('An SMTP To address is required to send a message. Set the message smtp_envelope_to, to, cc, or bcc address.')
     end
   end
-  
+
 end
diff --git a/spec/mail/network/delivery_methods/test_mailer_spec.rb b/spec/mail/network/delivery_methods/test_mailer_spec.rb
index 39c54cd98..18feabcc8 100644
--- a/spec/mail/network/delivery_methods/test_mailer_spec.rb
+++ b/spec/mail/network/delivery_methods/test_mailer_spec.rb
@@ -64,7 +64,7 @@
         subject "Email with no sender"
         body "body"
       end
-    end.should raise_error('A sender (Return-Path, Sender or From) required to send a message')
+    end.should raise_error('An SMTP From address is required to send a message. Set the message smtp_envelope_from, return_path, sender, or from address.')
   end
 
   it "should raise an error if no recipient if defined" do
@@ -77,7 +77,7 @@
         subject "Email with no recipient"
         body "body"
       end
-    end.should raise_error('At least one recipient (To, Cc or Bcc) is required to send a message')
+    end.should raise_error('An SMTP To address is required to send a message. Set the message smtp_envelope_to, to, cc, or bcc address.')
   end
 
 end