diff --git a/tests/handlers/test_send_email.py b/tests/handlers/test_send_email.py
index 6f77b1237c..da4bf8b582 100644
--- a/tests/handlers/test_send_email.py
+++ b/tests/handlers/test_send_email.py
@@ -23,7 +23,7 @@ from twisted.internet.defer import ensureDeferred
from twisted.mail import interfaces, smtp
from tests.server import FakeTransport
-from tests.unittest import HomeserverTestCase
+from tests.unittest import HomeserverTestCase, override_config
@implementer(interfaces.IMessageDelivery)
@@ -110,3 +110,58 @@ class SendEmailHandlerTestCase(HomeserverTestCase):
user, msg = message_delivery.messages.pop()
self.assertEqual(str(user), "foo@bar.com")
self.assertIn(b"Subject: test subject", msg)
+
+ @override_config(
+ {
+ "email": {
+ "notif_from": "noreply@test",
+ "force_tls": True,
+ },
+ }
+ )
+ def test_send_email_force_tls(self):
+ """Happy-path test that we can send email to an Implicit TLS server."""
+ h = self.hs.get_send_email_handler()
+ d = ensureDeferred(
+ h.send_email(
+ "foo@bar.com", "test subject", "Tests", "HTML content", "Text content"
+ )
+ )
+ # there should be an attempt to connect to localhost:465
+ self.assertEqual(len(self.reactor.sslClients), 1)
+ (
+ host,
+ port,
+ client_factory,
+ contextFactory,
+ _timeout,
+ _bindAddress,
+ ) = self.reactor.sslClients[0]
+ self.assertEqual(host, "localhost")
+ self.assertEqual(port, 465)
+
+ # wire it up to an SMTP server
+ message_delivery = _DummyMessageDelivery()
+ server_protocol = smtp.ESMTP()
+ server_protocol.delivery = message_delivery
+ # make sure that the server uses the test reactor to set timeouts
+ server_protocol.callLater = self.reactor.callLater # type: ignore[assignment]
+
+ client_protocol = client_factory.buildProtocol(None)
+ client_protocol.makeConnection(FakeTransport(server_protocol, self.reactor))
+ server_protocol.makeConnection(
+ FakeTransport(
+ client_protocol,
+ self.reactor,
+ peer_address=IPv4Address("TCP", "127.0.0.1", 1234),
+ )
+ )
+
+ # the message should now get delivered
+ self.get_success(d, by=0.1)
+
+ # check it arrived
+ self.assertEqual(len(message_delivery.messages), 1)
+ user, msg = message_delivery.messages.pop()
+ self.assertEqual(str(user), "foo@bar.com")
+ self.assertIn(b"Subject: test subject", msg)
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