1 files changed, 26 insertions, 4 deletions
diff --git a/Lib/test/test_smtpnet.py b/Lib/test/test_smtpnet.py
index e97cf363bb6..7f9db2ddf09 100644
--- a/Lib/test/test_smtpnet.py
+++ b/Lib/test/test_smtpnet.py
@@ -1,23 +1,35 @@
 import unittest
 from test import support
 import smtplib
+import socket
 
 ssl = support.import_module("ssl")
 
 support.requires("network")
 
+def check_ssl_verifiy(host, port):
+    context = ssl.create_default_context()
+    with socket.create_connection((host, port)) as sock:
+        try:
+            sock = context.wrap_socket(sock, server_hostname=host)
+        except Exception:
+            return False
+        else:
+            sock.close()
+            return True
+
 
 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')
+        context = ssl.SSLContext(ssl.PROTOCOL_SSLv23)
         with support.transient_internet(self.testServer):
             server = smtplib.SMTP(self.testServer, self.remotePort)
             try:
-                server.starttls(context=self.context)
+                server.starttls(context=context)
             except smtplib.SMTPException as e:
                 if e.args[0] == 'STARTTLS extension not supported by server.':
                     unittest.skip(e.args[0])
@@ -30,7 +42,7 @@ class SmtpTest(unittest.TestCase):
 class SmtpSSLTest(unittest.TestCase):
     testServer = 'smtp.gmail.com'
     remotePort = 465
-    context = ssl.SSLContext(ssl.PROTOCOL_SSLv23)
+    can_verify = check_ssl_verifiy(testServer, remotePort)
 
     def test_connect(self):
         support.get_attribute(smtplib, 'SMTP_SSL')
@@ -47,9 +59,19 @@ class SmtpSSLTest(unittest.TestCase):
             server.quit()
 
     def test_connect_using_sslcontext(self):
+        context = ssl.SSLContext(ssl.PROTOCOL_SSLv23)
+        support.get_attribute(smtplib, 'SMTP_SSL')
+        with support.transient_internet(self.testServer):
+            server = smtplib.SMTP_SSL(self.testServer, self.remotePort, context=context)
+            server.ehlo()
+            server.quit()
+
+    @unittest.skipUnless(can_verify, "SSL certificate can't be verified")
+    def test_connect_using_sslcontext_verified(self):
         support.get_attribute(smtplib, 'SMTP_SSL')
+        context = ssl.create_default_context()
         with support.transient_internet(self.testServer):
-            server = smtplib.SMTP_SSL(self.testServer, self.remotePort, context=self.context)
+            server = smtplib.SMTP_SSL(self.testServer, self.remotePort, context=context)
             server.ehlo()
             server.quit()