diff --git a/tests/handlers/test_send_email.py b/tests/handlers/test_send_email.py
deleted file mode 100644
index cedcea27d9..0000000000
--- a/tests/handlers/test_send_email.py
+++ /dev/null
@@ -1,230 +0,0 @@
-#
-# This file is licensed under the Affero General Public License (AGPL) version 3.
-#
-# Copyright 2021 The Matrix.org Foundation C.I.C.
-# Copyright (C) 2023 New Vector, Ltd
-#
-# This program is free software: you can redistribute it and/or modify
-# it under the terms of the GNU Affero General Public License as
-# published by the Free Software Foundation, either version 3 of the
-# License, or (at your option) any later version.
-#
-# See the GNU Affero General Public License for more details:
-# <https://www.gnu.org/licenses/agpl-3.0.html>.
-#
-# Originally licensed under the Apache License, Version 2.0:
-# <http://www.apache.org/licenses/LICENSE-2.0>.
-#
-# [This file includes modifications made by New Vector Limited]
-#
-#
-
-
-from typing import Callable, List, Tuple, Type, Union
-from unittest.mock import patch
-
-from zope.interface import implementer
-
-from twisted.internet import defer
-from twisted.internet._sslverify import ClientTLSOptions
-from twisted.internet.address import IPv4Address, IPv6Address
-from twisted.internet.defer import ensureDeferred
-from twisted.internet.interfaces import IProtocolFactory
-from twisted.internet.ssl import ContextFactory
-from twisted.mail import interfaces, smtp
-
-from tests.server import FakeTransport
-from tests.unittest import HomeserverTestCase, override_config
-
-
-def TestingESMTPTLSClientFactory(
- contextFactory: ContextFactory,
- _connectWrapped: bool,
- wrappedProtocol: IProtocolFactory,
-) -> IProtocolFactory:
- """We use this to pass through in testing without using TLS, but
- saving the context information to check that it would have happened.
-
- Note that this is what the MemoryReactor does on connectSSL.
- It only saves the contextFactory, but starts the connection with the
- underlying Factory.
- See: L{twisted.internet.testing.MemoryReactor.connectSSL}"""
-
- wrappedProtocol._testingContextFactory = contextFactory # type: ignore[attr-defined]
- return wrappedProtocol
-
-
-@implementer(interfaces.IMessageDelivery)
-class _DummyMessageDelivery:
- def __init__(self) -> None:
- # (recipient, message) tuples
- self.messages: List[Tuple[smtp.Address, bytes]] = []
-
- def receivedHeader(
- self,
- helo: Tuple[bytes, bytes],
- origin: smtp.Address,
- recipients: List[smtp.User],
- ) -> None:
- return None
-
- def validateFrom(
- self, helo: Tuple[bytes, bytes], origin: smtp.Address
- ) -> smtp.Address:
- return origin
-
- def record_message(self, recipient: smtp.Address, message: bytes) -> None:
- self.messages.append((recipient, message))
-
- def validateTo(self, user: smtp.User) -> Callable[[], interfaces.IMessageSMTP]:
- return lambda: _DummyMessage(self, user)
-
-
-@implementer(interfaces.IMessageSMTP)
-class _DummyMessage:
- """IMessageSMTP implementation which saves the message delivered to it
- to the _DummyMessageDelivery object.
- """
-
- def __init__(self, delivery: _DummyMessageDelivery, user: smtp.User):
- self._delivery = delivery
- self._user = user
- self._buffer: List[bytes] = []
-
- def lineReceived(self, line: bytes) -> None:
- self._buffer.append(line)
-
- def eomReceived(self) -> "defer.Deferred[bytes]":
- message = b"\n".join(self._buffer) + b"\n"
- self._delivery.record_message(self._user.dest, message)
- return defer.succeed(b"saved")
-
- def connectionLost(self) -> None:
- pass
-
-
-class SendEmailHandlerTestCaseIPv4(HomeserverTestCase):
- ip_class: Union[Type[IPv4Address], Type[IPv6Address]] = IPv4Address
-
- def setUp(self) -> None:
- super().setUp()
- self.reactor.lookups["localhost"] = "127.0.0.1"
-
- def test_send_email(self) -> None:
- """Happy-path test that we can send email to a non-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:25
- self.assertEqual(len(self.reactor.tcpClients), 1)
- (host, port, client_factory, _timeout, _bindAddress) = self.reactor.tcpClients[
- 0
- ]
- self.assertEqual(host, self.reactor.lookups["localhost"])
- self.assertEqual(port, 25)
-
- # 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=self.ip_class(
- "TCP", self.reactor.lookups["localhost"], 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)
-
- @patch(
- "synapse.handlers.send_email.TLSMemoryBIOFactory",
- TestingESMTPTLSClientFactory,
- )
- @override_config(
- {
- "email": {
- "notif_from": "noreply@test",
- "force_tls": True,
- },
- }
- )
- def test_send_email_force_tls(self) -> None:
- """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.tcpClients), 1)
- (
- host,
- port,
- client_factory,
- _timeout,
- _bindAddress,
- ) = self.reactor.tcpClients[0]
- self.assertEqual(host, self.reactor.lookups["localhost"])
- self.assertEqual(port, 465)
- # We need to make sure that TLS is happenning
- self.assertIsInstance(
- client_factory._wrappedFactory._testingContextFactory,
- ClientTLSOptions,
- )
- # And since we use endpoints, they go through reactor.connectTCP
- # which works differently to connectSSL on the testing reactor
-
- # 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=self.ip_class(
- "TCP", self.reactor.lookups["localhost"], 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)
-
-
-class SendEmailHandlerTestCaseIPv6(SendEmailHandlerTestCaseIPv4):
- ip_class = IPv6Address
-
- def setUp(self) -> None:
- super().setUp()
- self.reactor.lookups["localhost"] = "::1"
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