diff --git a/Lib/smtplib.py b/Lib/smtplib.py
index 7f49f23..6895bed 100755
--- a/Lib/smtplib.py
+++ b/Lib/smtplib.py
@@ -71,6 +71,13 @@
 class SMTPException(OSError):
     """Base class for all exceptions raised by this module."""
 
+class SMTPNotSupportedError(SMTPException):
+    """The command or option is not supported by the SMTP server.
+
+    This exception is raised when an attempt is made to run a command or a
+    command with an option which is not supported by the server.
+    """
+
 class SMTPServerDisconnected(SMTPException):
     """Not connected to any SMTP server.
 
@@ -237,6 +244,7 @@
         self._host = host
         self.timeout = timeout
         self.esmtp_features = {}
+        self.command_encoding = 'ascii'
         self.source_address = source_address
 
         if host:
@@ -337,7 +345,10 @@
             self._print_debug('send:', repr(s))
         if hasattr(self, 'sock') and self.sock:
             if isinstance(s, str):
-                s = s.encode("ascii")
+                # send is used by the 'data' command, where command_encoding
+                # should not be used, but 'data' needs to convert the string to
+                # binary itself anyway, so that's not a problem.
+                s = s.encode(self.command_encoding)
             try:
                 self.sock.sendall(s)
             except OSError:
@@ -482,6 +493,7 @@
 
     def rset(self):
         """SMTP 'rset' command -- resets session."""
+        self.command_encoding = 'ascii'
         return self.docmd("rset")
 
     def _rset(self):
@@ -501,9 +513,22 @@
         return self.docmd("noop")
 
     def mail(self, sender, options=[]):
-        """SMTP 'mail' command -- begins mail xfer session."""
+        """SMTP 'mail' command -- begins mail xfer session.
+
+        This method may raise the following exceptions:
+
+         SMTPNotSupportedError  The options parameter includes 'SMTPUTF8'
+                                but the SMTPUTF8 extension is not supported by
+                                the server.
+        """
         optionlist = ''
         if options and self.does_esmtp:
+            if any(x.lower()=='smtputf8' for x in options):
+                if self.has_extn('smtputf8'):
+                    self.command_encoding = 'utf-8'
+                else:
+                    raise SMTPNotSupportedError(
+                        'SMTPUTF8 not supported by server')
             optionlist = ' ' + ' '.join(options)
         self.putcmd("mail", "FROM:%s%s" % (quoteaddr(sender), optionlist))
         return self.getreply()
@@ -642,13 +667,16 @@
                                   the helo greeting.
          SMTPAuthenticationError  The server didn't accept the username/
                                   password combination.
+         SMTPNotSupportedError    The AUTH command is not supported by the
+                                  server.
          SMTPException            No suitable authentication method was
                                   found.
         """
 
         self.ehlo_or_helo_if_needed()
         if not self.has_extn("auth"):
-            raise SMTPException("SMTP AUTH extension not supported by server.")
+            raise SMTPNotSupportedError(
+                "SMTP AUTH extension not supported by server.")
 
         # Authentication methods the server claims to support
         advertised_authlist = self.esmtp_features["auth"].split()
@@ -700,7 +728,8 @@
         """
         self.ehlo_or_helo_if_needed()
         if not self.has_extn("starttls"):
-            raise SMTPException("STARTTLS extension not supported by server.")
+            raise SMTPNotSupportedError(
+                "STARTTLS extension not supported by server.")
         (resp, reply) = self.docmd("STARTTLS")
         if resp == 220:
             if not _have_ssl:
@@ -765,6 +794,9 @@
          SMTPDataError          The server replied with an unexpected
                                 error code (other than a refusal of
                                 a recipient).
+         SMTPNotSupportedError  The mail_options parameter includes 'SMTPUTF8'
+                                but the SMTPUTF8 extension is not supported by
+                                the server.
 
         Note: the connection will be open even after an exception is raised.
 
@@ -793,8 +825,6 @@
         if isinstance(msg, str):
             msg = _fix_eols(msg).encode('ascii')
         if self.does_esmtp:
-            # Hmmm? what's this? -ddm
-            # self.esmtp_features['7bit']=""
             if self.has_extn('size'):
                 esmtp_opts.append("size=%d" % len(msg))
             for option in mail_options:
diff --git a/Lib/test/test_smtplib.py b/Lib/test/test_smtplib.py
index 9011042..e496371 100644
--- a/Lib/test/test_smtplib.py
+++ b/Lib/test/test_smtplib.py
@@ -977,6 +977,125 @@
         self.assertIsNone(smtp.sock)
         self.assertEqual(self.serv._SMTPchannel.rcpt_count, 0)
 
+    def test_smtputf8_NotSupportedError_if_no_server_support(self):
+        smtp = smtplib.SMTP(
+            HOST, self.port, local_hostname='localhost', timeout=3)
+        self.addCleanup(smtp.close)
+        smtp.ehlo()
+        self.assertTrue(smtp.does_esmtp)
+        self.assertFalse(smtp.has_extn('smtputf8'))
+        self.assertRaises(
+            smtplib.SMTPNotSupportedError,
+            smtp.sendmail,
+            'John', 'Sally', '', mail_options=['BODY=8BITMIME', 'SMTPUTF8'])
+        self.assertRaises(
+            smtplib.SMTPNotSupportedError,
+            smtp.mail, 'John', options=['BODY=8BITMIME', 'SMTPUTF8'])
+
+    def test_send_unicode_without_SMTPUTF8(self):
+        smtp = smtplib.SMTP(
+            HOST, self.port, local_hostname='localhost', timeout=3)
+        self.addCleanup(smtp.close)
+        self.assertRaises(UnicodeEncodeError, smtp.sendmail, 'Alice', 'Böb', '')
+        self.assertRaises(UnicodeEncodeError, smtp.mail, 'Älice')
+
+
+class SimSMTPUTF8Server(SimSMTPServer):
+
+    def __init__(self, *args, **kw):
+        # The base SMTP server turns these on automatically, but our test
+        # server is set up to munge the EHLO response, so we need to provide
+        # them as well.  And yes, the call is to SMTPServer not SimSMTPServer.
+        self._extra_features = ['SMTPUTF8', '8BITMIME']
+        smtpd.SMTPServer.__init__(self, *args, **kw)
+
+    def handle_accepted(self, conn, addr):
+        self._SMTPchannel = self.channel_class(
+            self._extra_features, self, conn, addr,
+            decode_data=self._decode_data,
+            enable_SMTPUTF8=self.enable_SMTPUTF8,
+        )
+
+    def process_message(self, peer, mailfrom, rcpttos, data, mail_options=None,
+                                                             rcpt_options=None):
+        self.last_peer = peer
+        self.last_mailfrom = mailfrom
+        self.last_rcpttos = rcpttos
+        self.last_message = data
+        self.last_mail_options = mail_options
+        self.last_rcpt_options = rcpt_options
+
+
+@unittest.skipUnless(threading, 'Threading required for this test.')
+class SMTPUTF8SimTests(unittest.TestCase):
+
+    def setUp(self):
+        self.real_getfqdn = socket.getfqdn
+        socket.getfqdn = mock_socket.getfqdn
+        self.serv_evt = threading.Event()
+        self.client_evt = threading.Event()
+        # Pick a random unused port by passing 0 for the port number
+        self.serv = SimSMTPUTF8Server((HOST, 0), ('nowhere', -1),
+                                      decode_data=False,
+                                      enable_SMTPUTF8=True)
+        # Keep a note of what port was assigned
+        self.port = self.serv.socket.getsockname()[1]
+        serv_args = (self.serv, self.serv_evt, self.client_evt)
+        self.thread = threading.Thread(target=debugging_server, args=serv_args)
+        self.thread.start()
+
+        # wait until server thread has assigned a port number
+        self.serv_evt.wait()
+        self.serv_evt.clear()
+
+    def tearDown(self):
+        socket.getfqdn = self.real_getfqdn
+        # indicate that the client is finished
+        self.client_evt.set()
+        # wait for the server thread to terminate
+        self.serv_evt.wait()
+        self.thread.join()
+
+    def test_test_server_supports_extensions(self):
+        smtp = smtplib.SMTP(
+            HOST, self.port, local_hostname='localhost', timeout=3)
+        self.addCleanup(smtp.close)
+        smtp.ehlo()
+        self.assertTrue(smtp.does_esmtp)
+        self.assertTrue(smtp.has_extn('smtputf8'))
+
+    def test_send_unicode_with_SMTPUTF8_via_sendmail(self):
+        m = '¡a test message containing unicode!'.encode('utf-8')
+        smtp = smtplib.SMTP(
+            HOST, self.port, local_hostname='localhost', timeout=3)
+        self.addCleanup(smtp.close)
+        smtp.sendmail('Jőhn', 'Sálly', m,
+                      mail_options=['BODY=8BITMIME', 'SMTPUTF8'])
+        self.assertEqual(self.serv.last_mailfrom, 'Jőhn')
+        self.assertEqual(self.serv.last_rcpttos, ['Sálly'])
+        self.assertEqual(self.serv.last_message, m)
+        self.assertIn('BODY=8BITMIME', self.serv.last_mail_options)
+        self.assertIn('SMTPUTF8', self.serv.last_mail_options)
+        self.assertEqual(self.serv.last_rcpt_options, [])
+
+    def test_send_unicode_with_SMTPUTF8_via_low_level_API(self):
+        m = '¡a test message containing unicode!'.encode('utf-8')
+        smtp = smtplib.SMTP(
+            HOST, self.port, local_hostname='localhost', timeout=3)
+        self.addCleanup(smtp.close)
+        smtp.ehlo()
+        self.assertEqual(
+            smtp.mail('Jő', options=['BODY=8BITMIME', 'SMTPUTF8']),
+            (250, b'OK'))
+        self.assertEqual(smtp.rcpt('János'), (250, b'OK'))
+        self.assertEqual(smtp.data(m), (250, b'OK'))
+        self.assertEqual(self.serv.last_mailfrom, 'Jő')
+        self.assertEqual(self.serv.last_rcpttos, ['János'])
+        self.assertEqual(self.serv.last_message, m)
+        self.assertIn('BODY=8BITMIME', self.serv.last_mail_options)
+        self.assertIn('SMTPUTF8', self.serv.last_mail_options)
+        self.assertEqual(self.serv.last_rcpt_options, [])
+
 
 @support.reap_threads
 def test_main(verbose=None):