1 files changed, 37 insertions, 7 deletions
diff --git a/Lib/test/test_smtpnet.py b/Lib/test/test_smtpnet.py
index 0198ab669e..e97cf363bb 100644
--- a/Lib/test/test_smtpnet.py
+++ b/Lib/test/test_smtpnet.py
@@ -1,31 +1,61 @@
-#!/usr/bin/env python3
-
 import unittest
 from test import support
 import smtplib
 
+ssl = support.import_module("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)
+            try:
+                server.starttls(context=self.context)
+            except smtplib.SMTPException as e:
+                if e.args[0] == 'STARTTLS extension not supported by server.':
+                    unittest.skip(e.args[0])
+                else:
+                    raise
+            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')
         with support.transient_internet(self.testServer):
             server = smtplib.SMTP_SSL(self.testServer, self.remotePort)
-        server.ehlo()
-        server.quit()
+            server.ehlo()
+            server.quit()
 
     def test_connect_default_port(self):
         support.get_attribute(smtplib, 'SMTP_SSL')
         with support.transient_internet(self.testServer):
             server = smtplib.SMTP_SSL(self.testServer)
-        server.ehlo()
-        server.quit()
+            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()