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@@ -6,16 +6,16 @@ Net::SMTP.class_eval do
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     raise IOError, 'SMTP session already started' if @started
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     check_auth_args user, secret, authtype if user or secret
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-    socket = timeout(@open_timeout) { TCPSocket.open(@address, @port) }
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-    @socket = Net::InternetMessageIO.new(socket)
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-    @socket.read_timeout = 60 #@read_timeout
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-    @socket.debug_output = STDERR #@debug_output
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+    open_conversation(helodomain)
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-    check_response(critical { recv_response() })
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-    do_helo(helodomain)
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-
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-
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-    create_ssl_socket(socket, helodomain) if starttls
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+    if starttls
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+      create_ssl_socket(socket, helodomain)
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+    else
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+      # some SMTP servers that don't support TLS drop the socket after rejecting
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+      # STARTTLS command, so reopen the conversation
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+      @socket.close
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+      open_conversation(helodomain)
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+    end
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     authenticate user, secret, authtype if user
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     @started = true
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@@ -53,9 +53,9 @@ Net::SMTP.class_eval do
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     end
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   end
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-  def create_ssl_socket(underlying_socket, helodomain)
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+  def create_ssl_socket(helodomain)
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     require "openssl"
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-    ssl = OpenSSL::SSL::SSLSocket.new(underlying_socket)
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+    ssl = OpenSSL::SSL::SSLSocket.new(@tcp_socket)
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     ssl.sync_close = true
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     ssl.connect
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     @socket = Net::InternetMessageIO.new(ssl)
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@@ -64,6 +64,16 @@ Net::SMTP.class_eval do
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     do_helo(helodomain)
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   end
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+  def open_conversation(helodomain)
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+    @tcp_socket = timeout(@open_timeout) { TCPSocket.open(@address, @port) }
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+    @socket = Net::InternetMessageIO.new(@tcp_socket)
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+    @socket.read_timeout = 60 #@read_timeout
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+    @socket.debug_output = STDERR #@debug_output
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+
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+    check_response(critical { recv_response() })
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+    do_helo(helodomain)
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+  end
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+
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   def quit
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     begin
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       getok('QUIT')
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@@ -71,4 +81,4 @@ Net::SMTP.class_eval do
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     end
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   end
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-end
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\ No newline at end of file
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+end