diff --git a/flask_mailman/backends/smtp.py b/flask_mailman/backends/smtp.py
index ceb60ee..4198b49 100644
--- a/flask_mailman/backends/smtp.py
+++ b/flask_mailman/backends/smtp.py
@@ -3,6 +3,8 @@
 import ssl
 import threading
 
+from werkzeug.utils import cached_property
+
 from flask_mailman.backends.base import BaseEmailBackend
 from flask_mailman.message import sanitize_address
 from flask_mailman.utils import DNS_NAME
@@ -48,6 +50,15 @@ def __init__(
     def connection_class(self):
         return smtplib.SMTP_SSL if self.use_ssl else smtplib.SMTP
 
+    @cached_property
+    def ssl_context(self):
+        if self.ssl_certfile or self.ssl_keyfile:
+            ssl_context = ssl.SSLContext(protocol=ssl.PROTOCOL_TLS_CLIENT)
+            ssl_context.load_cert_chain(self.ssl_certfile, self.ssl_keyfile)
+            return ssl_context
+        else:
+            return ssl.create_default_context()
+
     def open(self):
         """
         Ensure an open connection to the email server. Return whether or not a
@@ -64,12 +75,7 @@ def open(self):
         if self.timeout is not None:
             connection_params['timeout'] = self.timeout
         if self.use_ssl:
-            connection_params.update(
-                {
-                    'keyfile': self.ssl_keyfile,
-                    'certfile': self.ssl_certfile,
-                }
-            )
+            connection_params["context"] = self.ssl_context
         try:
             self.connection = self.connection_class(self.host, self.port, **connection_params)
 
diff --git a/tests/test_backend.py b/tests/test_backend.py
index 425be08..7a5418f 100644
--- a/tests/test_backend.py
+++ b/tests/test_backend.py
@@ -2,7 +2,9 @@
 from email.utils import parseaddr
 import os
 import socket
+from ssl import SSLError
 import tempfile
+from unittest import mock
 import pytest
 
 from pathlib import Path
@@ -341,6 +343,41 @@ def test_email_tls_attempts_starttls(self):
                 with backend:
                     pass
 
+    def test_email_ssl_attempts_ssl_connection(self):
+        fake_keyfile = os.path.join(os.path.dirname(__file__), "attachments", 'file.txt')
+        fake_certfile = os.path.join(os.path.dirname(__file__), "attachments", 'file_txt')
+        with SmtpdContext(self.app.extensions['mailman']):
+            self.app.extensions['mailman'].use_ssl = True
+            self.app.extensions['mailman'].ssl_keyfile = fake_keyfile
+            self.app.extensions['mailman'].ssl_certfile = fake_certfile
+
+            backend = smtp.EmailBackend()
+            self.assertTrue(backend.use_ssl)
+            with self.assertRaises(SSLError):
+                with backend:
+                    pass
+
+    @mock.patch("ssl.SSLContext.load_cert_chain", return_value="")
+    def test_email_ssl_cached_context(self, result_mocked):
+        fake_keyfile = os.path.join(os.path.dirname(__file__), "attachments", 'file.txt')
+        fake_certfile = os.path.join(os.path.dirname(__file__), "attachments", 'file_txt')
+
+        with SmtpdContext(self.app.extensions['mailman']):
+            self.app.extensions['mailman'].use_ssl = True
+
+            backend_one = smtp.EmailBackend()
+            backend_another = smtp.EmailBackend()
+
+            self.assertTrue(backend_one.ssl_context, backend_another.ssl_context)
+
+            self.app.extensions['mailman'].ssl_keyfile = fake_keyfile
+            self.app.extensions['mailman'].ssl_certfile = fake_certfile
+
+            backend_one = smtp.EmailBackend()
+            backend_another = smtp.EmailBackend()
+
+            self.assertTrue(backend_one.ssl_context, backend_another.ssl_context)
+
     def test_connection_timeout_default(self):
         """The connection's timeout value is None by default."""
         self.app.extensions['mailman'].backend = "smtp"