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()