diff --git a/Doc/library/smtplib.rst b/Doc/library/smtplib.rst
index cfd5018..b432d3e 100644
--- a/Doc/library/smtplib.rst
+++ b/Doc/library/smtplib.rst
@@ -49,7 +49,7 @@
       Support for the :keyword:`with` statement was added.
 
 
-.. class:: SMTP_SSL(host='', port=0, local_hostname=None, keyfile=None, certfile=None[, timeout])
+.. class:: SMTP_SSL(host='', port=0, local_hostname=None, keyfile=None, certfile=None[, timeout], context=None)
 
    A :class:`SMTP_SSL` instance behaves exactly the same as instances of
    :class:`SMTP`. :class:`SMTP_SSL` should be used for situations where SSL is
@@ -57,11 +57,16 @@
    not appropriate. If *host* is not specified, the local host is used. If
    *port* is zero, the standard SMTP-over-SSL port (465) is used. *keyfile*
    and *certfile* are also optional, and can contain a PEM formatted private key
-   and certificate chain file for the SSL connection. The optional *timeout*
+   and certificate chain file for the SSL connection. *context* also optional, can contain
+   a SSLContext, and is an alternative to keyfile and certfile; If it is specified both
+   keyfile and certfile must be None.  The optional *timeout*
    parameter specifies a timeout in seconds for blocking operations like the
    connection attempt (if not specified, the global default timeout setting
    will be used).
 
+   .. versionchanged:: 3.3
+      *context* was added.
+
 
 .. class:: LMTP(host='', port=LMTP_PORT, local_hostname=None)
 
@@ -256,7 +261,7 @@
       No suitable authentication method was found.
 
 
-.. method:: SMTP.starttls(keyfile=None, certfile=None)
+.. method:: SMTP.starttls(keyfile=None, certfile=None, context=None)
 
    Put the SMTP connection in TLS (Transport Layer Security) mode.  All SMTP
    commands that follow will be encrypted.  You should then call :meth:`ehlo`
@@ -265,6 +270,9 @@
    If *keyfile* and *certfile* are provided, these are passed to the :mod:`socket`
    module's :func:`ssl` function.
 
+   Optional *context* parameter is a :class:`ssl.SSLContext` object; This is an alternative to
+   using a keyfile and a certfile and if specified both *keyfile* and *certfile* should be None.
+
    If there has been no previous ``EHLO`` or ``HELO`` command this session,
    this method tries ESMTP ``EHLO`` first.
 
@@ -277,6 +285,9 @@
    :exc:`RuntimeError`
      SSL/TLS support is not available to your Python interpreter.
 
+   .. versionchanged:: 3.3
+      *context* was added.
+
 
 .. method:: SMTP.sendmail(from_addr, to_addrs, msg, mail_options=[], rcpt_options=[])
 
diff --git a/Lib/smtplib.py b/Lib/smtplib.py
index 15294ff..f724b9f 100755
--- a/Lib/smtplib.py
+++ b/Lib/smtplib.py
@@ -635,7 +635,7 @@
         # We could not login sucessfully. Return result of last attempt.
         raise SMTPAuthenticationError(code, resp)
 
-    def starttls(self, keyfile=None, certfile=None):
+    def starttls(self, keyfile=None, certfile=None, context=None):
         """Puts the connection to the SMTP server into TLS mode.
 
         If there has been no previous EHLO or HELO command this session, this
@@ -659,7 +659,16 @@
         if resp == 220:
             if not _have_ssl:
                 raise RuntimeError("No SSL support included in this Python")
-            self.sock = ssl.wrap_socket(self.sock, keyfile, certfile)
+            if context is not None and keyfile is not None:
+                raise ValueError("context and keyfile arguments are mutually "
+                                 "exclusive")
+            if context is not None and certfile is not None:
+                raise ValueError("context and certfile arguments are mutually "
+                                 "exclusive")
+            if context is not None:
+                self.sock = context.wrap_socket(self.sock)
+            else:
+                self.sock = ssl.wrap_socket(self.sock, keyfile, certfile)
             self.file = SSLFakeFile(self.sock)
             # RFC 3207:
             # The client MUST discard any knowledge obtained from
@@ -815,23 +824,35 @@
         support). If host is not specified, '' (the local host) is used. If port is
         omitted, the standard SMTP-over-SSL port (465) is used. keyfile and certfile
         are also optional - they can contain a PEM formatted private key and
-        certificate chain file for the SSL connection.
+        certificate chain file for the SSL connection. context also optional, can contain
+        a SSLContext, and is an alternative to keyfile and certfile; If it is specified both
+        keyfile and certfile must be None.
         """
 
         default_port = SMTP_SSL_PORT
 
         def __init__(self, host='', port=0, local_hostname=None,
                      keyfile=None, certfile=None,
-                     timeout=socket._GLOBAL_DEFAULT_TIMEOUT):
+                     timeout=socket._GLOBAL_DEFAULT_TIMEOUT, context=None):
+            if context is not None and keyfile is not None:
+                raise ValueError("context and keyfile arguments are mutually "
+                                 "exclusive")
+            if context is not None and certfile is not None:
+                raise ValueError("context and certfile arguments are mutually "
+                                 "exclusive")
             self.keyfile = keyfile
             self.certfile = certfile
+            self.context = context
             SMTP.__init__(self, host, port, local_hostname, timeout)
 
         def _get_socket(self, host, port, timeout):
             if self.debuglevel > 0:
                 print('connect:', (host, port), file=stderr)
             new_socket = socket.create_connection((host, port), timeout)
-            new_socket = ssl.wrap_socket(new_socket, self.keyfile, self.certfile)
+            if self.context is not None:
+                new_socket = self.context.wrap_socket(new_socket)
+            else:
+                new_socket = ssl.wrap_socket(new_socket, self.keyfile, self.certfile)
             self.file = SSLFakeFile(new_socket)
             return new_socket
 
diff --git a/Lib/test/test_smtpnet.py b/Lib/test/test_smtpnet.py
index 0198ab6..ca31c1e 100644
--- a/Lib/test/test_smtpnet.py
+++ b/Lib/test/test_smtpnet.py
@@ -3,12 +3,29 @@
 import unittest
 from test import support
 import smtplib
+import ssl
 
 support.requires("network")
 
+
+class SmtpTest(unittest.TestCase):
+    testServer = 'smtp.gmail.com'
+    remotePort = 25
+    context = ssl.SSLContext(ssl.PROTOCOL_SSLv23)
+
+    def test_connect_starttls(self):
+        support.get_attribute(smtplib, 'SMTP_SSL')
+        with support.transient_internet(self.testServer):
+            server = smtplib.SMTP(self.testServer, self.remotePort)
+            server.starttls(context=self.context)
+        server.ehlo()
+        server.quit()
+
+
 class SmtpSSLTest(unittest.TestCase):
     testServer = 'smtp.gmail.com'
     remotePort = 465
+    context = ssl.SSLContext(ssl.PROTOCOL_SSLv23)
 
     def test_connect(self):
         support.get_attribute(smtplib, 'SMTP_SSL')
@@ -24,8 +41,16 @@
         server.ehlo()
         server.quit()
 
+    def test_connect_using_sslcontext(self):
+        support.get_attribute(smtplib, 'SMTP_SSL')
+        with support.transient_internet(self.testServer):
+            server = smtplib.SMTP_SSL(self.testServer, self.remotePort, context=self.context)
+        server.ehlo()
+        server.quit()
+
+
 def test_main():
-    support.run_unittest(SmtpSSLTest)
+    support.run_unittest(SmtpTest, SmtpSSLTest)
 
 if __name__ == "__main__":
     test_main()
diff --git a/Misc/NEWS b/Misc/NEWS
index ae98b9b..901250f 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -153,6 +153,10 @@
 Library
 -------
 
+- Issue #8809: The SMTP_SSL constructor and SMTP.starttls() now support
+  passing a ``context`` argument pointing to an ssl.SSLContext instance.
+  Patch by Kasun Herath.
+
 - Issue #11088: don't crash when using F5 to run a script in IDLE on MacOSX
   with Tk 8.5.