Support Implicit TLS for sending emails (#13317)

Previously, TLS could only be used with STARTTLS.
Add a new option `force_tls`, where TLS is used from the start.
Implicit TLS is recommended over STARTLS,
see https://datatracker.ietf.org/doc/html/rfc8314

Fixes #8046.

Signed-off-by: Jan Schär <jan@jschaer.ch>

5 files changed, 99 insertions, 13 deletions

diff --git a/changelog.d/13317.feature b/changelog.d/13317.feature
new file mode 100644
index 0000000000..e0ebd2b51f
--- /dev/null
+++ b/changelog.d/13317.feature
@@ -0,0 +1 @@
+Support Implicit TLS for sending emails, enabled by the new option `force_tls`. Contributed by Jan Schär.
diff --git a/docs/usage/configuration/config_documentation.md b/docs/usage/configuration/config_documentation.md
index a10f6662eb..eefcc7829d 100644
--- a/docs/usage/configuration/config_documentation.md
+++ b/docs/usage/configuration/config_documentation.md
@@ -3187,9 +3187,17 @@ Server admins can configure custom templates for email content. See
 
 This setting has the following sub-options:
 * `smtp_host`: The hostname of the outgoing SMTP server to use. Defaults to 'localhost'.
-* `smtp_port`: The port on the mail server for outgoing SMTP. Defaults to 25.
+* `smtp_port`: The port on the mail server for outgoing SMTP. Defaults to 465 if `force_tls` is true, else 25.
+  
+  _Changed in Synapse 1.64.0:_ the default port is now aware of `force_tls`.
 * `smtp_user` and `smtp_pass`: Username/password for authentication to the SMTP server. By default, no
    authentication is attempted.
+* `force_tls`: By default, Synapse connects over plain text and then optionally upgrades
+   to TLS via STARTTLS. If this option is set to true, TLS is used from the start (Implicit TLS),
+   and the option `require_transport_security` is ignored.
+   It is recommended to enable this if supported by your mail server.
+  
+  _New in Synapse 1.64.0._
 * `require_transport_security`: Set to true to require TLS transport security for SMTP.
    By default, Synapse will connect over plain text, and will then switch to
    TLS via STARTTLS *if the SMTP server supports it*. If this option is set,
@@ -3254,6 +3262,7 @@ email:
   smtp_port: 587
   smtp_user: "exampleusername"
   smtp_pass: "examplepassword"
+  force_tls: true
   require_transport_security: true
   enable_tls: false
   notif_from: "Your Friendly %(app)s homeserver <noreply@example.com>"
diff --git a/synapse/config/emailconfig.py b/synapse/config/emailconfig.py
index 3ead80d985..73b469f414 100644
--- a/synapse/config/emailconfig.py
+++ b/synapse/config/emailconfig.py
@@ -85,14 +85,19 @@ class EmailConfig(Config):
         if email_config is None:
             email_config = {}
 
+        self.force_tls = email_config.get("force_tls", False)
         self.email_smtp_host = email_config.get("smtp_host", "localhost")
-        self.email_smtp_port = email_config.get("smtp_port", 25)
+        self.email_smtp_port = email_config.get(
+            "smtp_port", 465 if self.force_tls else 25
+        )
         self.email_smtp_user = email_config.get("smtp_user", None)
         self.email_smtp_pass = email_config.get("smtp_pass", None)
         self.require_transport_security = email_config.get(
             "require_transport_security", False
         )
         self.enable_smtp_tls = email_config.get("enable_tls", True)
+        if self.force_tls and not self.enable_smtp_tls:
+            raise ConfigError("email.force_tls requires email.enable_tls to be true")
         if self.require_transport_security and not self.enable_smtp_tls:
             raise ConfigError(
                 "email.require_transport_security requires email.enable_tls to be true"
diff --git a/synapse/handlers/send_email.py b/synapse/handlers/send_email.py
index a305a66860..e2844799e8 100644
--- a/synapse/handlers/send_email.py
+++ b/synapse/handlers/send_email.py
@@ -23,10 +23,12 @@ from pkg_resources import parse_version
 
 import twisted
 from twisted.internet.defer import Deferred
-from twisted.internet.interfaces import IOpenSSLContextFactory, IReactorTCP
+from twisted.internet.interfaces import IOpenSSLContextFactory
+from twisted.internet.ssl import optionsForClientTLS
 from twisted.mail.smtp import ESMTPSender, ESMTPSenderFactory
 
 from synapse.logging.context import make_deferred_yieldable
+from synapse.types import ISynapseReactor
 
 if TYPE_CHECKING:
     from synapse.server import HomeServer
@@ -48,7 +50,7 @@ class _NoTLSESMTPSender(ESMTPSender):
 
 
 async def _sendmail(
-    reactor: IReactorTCP,
+    reactor: ISynapseReactor,
     smtphost: str,
     smtpport: int,
     from_addr: str,
@@ -59,6 +61,7 @@ async def _sendmail(
     require_auth: bool = False,
     require_tls: bool = False,
     enable_tls: bool = True,
+    force_tls: bool = False,
 ) -> None:
     """A simple wrapper around ESMTPSenderFactory, to allow substitution in tests
 
@@ -73,8 +76,9 @@ async def _sendmail(
         password: password to give when authenticating
         require_auth: if auth is not offered, fail the request
         require_tls: if TLS is not offered, fail the reqest
-        enable_tls: True to enable TLS. If this is False and require_tls is True,
+        enable_tls: True to enable STARTTLS. If this is False and require_tls is True,
            the request will fail.
+        force_tls: True to enable Implicit TLS.
     """
     msg = BytesIO(msg_bytes)
     d: "Deferred[object]" = Deferred()
@@ -105,13 +109,23 @@ async def _sendmail(
         # set to enable TLS.
         factory = build_sender_factory(hostname=smtphost if enable_tls else None)
 
-    reactor.connectTCP(
-        smtphost,
-        smtpport,
-        factory,
-        timeout=30,
-        bindAddress=None,
-    )
+    if force_tls:
+        reactor.connectSSL(
+            smtphost,
+            smtpport,
+            factory,
+            optionsForClientTLS(smtphost),
+            timeout=30,
+            bindAddress=None,
+        )
+    else:
+        reactor.connectTCP(
+            smtphost,
+            smtpport,
+            factory,
+            timeout=30,
+            bindAddress=None,
+        )
 
     await make_deferred_yieldable(d)
 
@@ -132,6 +146,7 @@ class SendEmailHandler:
         self._smtp_pass = passwd.encode("utf-8") if passwd is not None else None
         self._require_transport_security = hs.config.email.require_transport_security
         self._enable_tls = hs.config.email.enable_smtp_tls
+        self._force_tls = hs.config.email.force_tls
 
         self._sendmail = _sendmail
 
@@ -189,4 +204,5 @@ class SendEmailHandler:
             require_auth=self._smtp_user is not None,
             require_tls=self._require_transport_security,
             enable_tls=self._enable_tls,
+            force_tls=self._force_tls,
         )
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)