Tests for SSL certs for federation connections

Add some tests for bad certificates for federation and .well-known connections

6 files changed, 343 insertions, 106 deletions

diff --git a/tests/http/__init__.py b/tests/http/__init__.py
index 851fc0eb33..b03fff0945 100644
--- a/tests/http/__init__.py
+++ b/tests/http/__init__.py
@@ -13,28 +13,124 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import os.path
+import subprocess
+
+from zope.interface import implementer
 
 from OpenSSL import SSL
+from OpenSSL.SSL import Connection
+from twisted.internet.interfaces import IOpenSSLServerConnectionCreator
+
+
+def get_test_ca_cert_file():
+    """Get the path to the test CA cert
+
+    The keypair is generated with:
+
+        openssl genrsa -out ca.key 2048
+        openssl req -new -x509 -key ca.key -days 3650 -out ca.crt \
+            -subj '/CN=synapse test CA'
+    """
+    return os.path.join(os.path.dirname(__file__), "ca.crt")
+
+
+def get_test_key_file():
+    """get the path to the test key
+
+    The key file is made with:
+
+        openssl genrsa -out server.key 2048
+    """
+    return os.path.join(os.path.dirname(__file__), "server.key")
+
+
+cert_file_count = 0
+
+CONFIG_TEMPLATE = b"""\
+[default]
+basicConstraints = CA:FALSE
+keyUsage=nonRepudiation, digitalSignature, keyEncipherment
+subjectAltName = %(sanentries)b
+"""
+
+
+def create_test_cert_file(sanlist):
+    """build an x509 certificate file
+
+    Args:
+        sanlist: list[bytes]: a list of subjectAltName values for the cert
+
+    Returns:
+        str: the path to the file
+    """
+    global cert_file_count
+    csr_filename = "server.csr"
+    cnf_filename = "server.%i.cnf" % (cert_file_count,)
+    cert_filename = "server.%i.crt" % (cert_file_count,)
+    cert_file_count += 1
+
+    # first build a CSR
+    subprocess.run(
+        [
+            "openssl",
+            "req",
+            "-new",
+            "-key",
+            get_test_key_file(),
+            "-subj",
+            "/",
+            "-out",
+            csr_filename,
+        ],
+        check=True,
+    )
 
+    # now a config file describing the right SAN entries
+    sanentries = b",".join(sanlist)
+    with open(cnf_filename, "wb") as f:
+        f.write(CONFIG_TEMPLATE % {b"sanentries": sanentries})
 
-def get_test_cert_file():
-    """get the path to the test cert"""
+    # finally the cert
+    ca_key_filename = os.path.join(os.path.dirname(__file__), "ca.key")
+    ca_cert_filename = get_test_ca_cert_file()
+    subprocess.run(
+        [
+            "openssl",
+            "x509",
+            "-req",
+            "-in",
+            csr_filename,
+            "-CA",
+            ca_cert_filename,
+            "-CAkey",
+            ca_key_filename,
+            "-set_serial",
+            "1",
+            "-extfile",
+            cnf_filename,
+            "-out",
+            cert_filename,
+        ],
+        check=True,
+    )
 
-    # the cert file itself is made with:
-    #
-    # openssl req -x509 -newkey rsa:4096 -keyout server.pem  -out server.pem -days 36500 \
-    #     -nodes -subj '/CN=testserv'
-    return os.path.join(os.path.dirname(__file__), 'server.pem')
+    return cert_filename
 
 
-class ServerTLSContext(object):
-    """A TLS Context which presents our test cert."""
+@implementer(IOpenSSLServerConnectionCreator)
+class TestServerTLSConnectionFactory(object):
+    """An SSL connection creator which returns connections which present a certificate
+    signed by our test CA."""
 
-    def __init__(self):
-        self.filename = get_test_cert_file()
+    def __init__(self, sanlist):
+        """
+        Args:
+            sanlist: list[bytes]: a list of subjectAltName values for the cert
+        """
+        self._cert_file = create_test_cert_file(sanlist)
 
-    def getContext(self):
+    def serverConnectionForTLS(self, tlsProtocol):
         ctx = SSL.Context(SSL.TLSv1_METHOD)
-        ctx.use_certificate_file(self.filename)
-        ctx.use_privatekey_file(self.filename)
-        return ctx
+        ctx.use_certificate_file(self._cert_file)
+        ctx.use_privatekey_file(get_test_key_file())
+        return Connection(ctx, None)
diff --git a/tests/http/ca.crt b/tests/http/ca.crt
new file mode 100644
index 0000000000..730f81e99c
--- /dev/null
+++ b/tests/http/ca.crt
@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/tests/http/ca.key b/tests/http/ca.key
new file mode 100644
index 0000000000..5c99cae186
--- /dev/null
+++ b/tests/http/ca.key
@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----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+pQy4dX7/Oe6NLAR1UEQjXmCuXf+rxnxF3VJd1nRxAoGBANb9eusl9fusgSnVOTjJ
+AQ7V36KVRv9hZoG6liBNwo80zDVmms4JhRd1MBkd3mkMkzIF4SkZUnWlwLBSANGM
+dX/3eZ5i1AVwgF5Am/f5TNxopDbdT/o1RVT/P8dcFT7s1xuBn+6wU0F7dFBgWqVu
+lt4aY85zNrJcj5XBHhqwdDGLAoGBAIksPNUAy9F3m5C6ih8o/aKAQx5KIeXrBUZq
+v43tK+kbYfRJHBjHWMOBbuxq0G/VmGPf9q9GtGqGXuxZG+w+rYtJx1OeMQZShjIZ
+ITl5CYeahrXtK4mo+fF2PMh3m5UE861LWuKKWhPwpJiWXC5grDNcjlHj1pcTdeip
+PjHkuJPhAoGBAIh35DptqqdicOd3dr/+/m2YQywY8aSpMrR0bC06aAkscD7oq4tt
+s/jwl0UlHIrEm/aMN7OnGIbpfkVdExfGKYaa5NRlgOwQpShwLufIo/c8fErd2zb8
+K3ptlwBxMrayMXpS3DP78r83Z0B8/FSK2guelzdRJ3ftipZ9io1Gss1C
+-----END RSA PRIVATE KEY-----
diff --git a/tests/http/federation/test_matrix_federation_agent.py b/tests/http/federation/test_matrix_federation_agent.py
index 05880a1048..ecce473b01 100644
--- a/tests/http/federation/test_matrix_federation_agent.py
+++ b/tests/http/federation/test_matrix_federation_agent.py
@@ -17,12 +17,14 @@ import logging
 from mock import Mock
 
 import treq
+from service_identity import VerificationError
 from zope.interface import implementer
 
 from twisted.internet import defer
 from twisted.internet._sslverify import ClientTLSOptions, OpenSSLCertificateOptions
 from twisted.internet.protocol import Factory
 from twisted.protocols.tls import TLSMemoryBIOFactory
+from twisted.web._newclient import ResponseNeverReceived
 from twisted.web.http import HTTPChannel
 from twisted.web.http_headers import Headers
 from twisted.web.iweb import IPolicyForHTTPS
@@ -37,13 +39,29 @@ from synapse.http.federation.srv_resolver import Server
 from synapse.util.caches.ttlcache import TTLCache
 from synapse.util.logcontext import LoggingContext
 
-from tests.http import ServerTLSContext
+from tests.http import TestServerTLSConnectionFactory, get_test_ca_cert_file
 from tests.server import FakeTransport, ThreadedMemoryReactorClock
 from tests.unittest import TestCase
 from tests.utils import default_config
 
 logger = logging.getLogger(__name__)
 
+test_server_connection_factory = None
+
+
+def get_connection_factory():
+    # this needs to happen once, but not until we are ready to run the first test
+    global test_server_connection_factory
+    if test_server_connection_factory is None:
+        test_server_connection_factory = TestServerTLSConnectionFactory(sanlist=[
+            b'DNS:testserv',
+            b'DNS:target-server',
+            b'DNS:xn--bcher-kva.com',
+            b'IP:1.2.3.4',
+            b'IP:::1',
+        ])
+    return test_server_connection_factory
+
 
 class MatrixFederationAgentTests(TestCase):
     def setUp(self):
@@ -53,12 +71,11 @@ class MatrixFederationAgentTests(TestCase):
 
         self.well_known_cache = TTLCache("test_cache", timer=self.reactor.seconds)
 
-        # for now, we disable cert verification for the test, since the cert we
-        # present will not be trusted. We should do better here, though.
         config_dict = default_config("test", parse=False)
-        config_dict["federation_verify_certificates"] = False
-        config_dict["trusted_key_servers"] = []
-        config = HomeServerConfig()
+        config_dict["federation_custom_ca_list"] = [get_test_ca_cert_file()]
+        # config_dict["trusted_key_servers"] = []
+
+        self._config = config = HomeServerConfig()
         config.parse_config_dict(config_dict)
 
         self.agent = MatrixFederationAgent(
@@ -77,7 +94,7 @@ class MatrixFederationAgentTests(TestCase):
         """
 
         # build the test server
-        server_tls_protocol = _build_test_server()
+        server_tls_protocol = _build_test_server(get_connection_factory())
 
         # now, tell the client protocol factory to build the client protocol (it will be a
         # _WrappingProtocol, around a TLSMemoryBIOProtocol, around an
@@ -328,6 +345,88 @@ class MatrixFederationAgentTests(TestCase):
         self.reactor.pump((0.1,))
         self.successResultOf(test_d)
 
+    def test_get_hostname_bad_cert(self):
+        """
+        Test the behaviour when the certificate on the server doesn't match the hostname
+        """
+        self.mock_resolver.resolve_service.side_effect = lambda _: []
+        self.reactor.lookups["testserv1"] = "1.2.3.4"
+
+        test_d = self._make_get_request(b"matrix://testserv1/foo/bar")
+
+        # Nothing happened yet
+        self.assertNoResult(test_d)
+
+        # No SRV record lookup yet
+        self.mock_resolver.resolve_service.assert_not_called()
+
+        # there should be an attempt to connect on port 443 for the .well-known
+        clients = self.reactor.tcpClients
+        self.assertEqual(len(clients), 1)
+        (host, port, client_factory, _timeout, _bindAddress) = clients[0]
+        self.assertEqual(host, '1.2.3.4')
+        self.assertEqual(port, 443)
+
+        # fonx the connection
+        client_factory.clientConnectionFailed(None, Exception("nope"))
+
+        # attemptdelay on the hostnameendpoint is 0.3, so takes that long before the
+        # .well-known request fails.
+        self.reactor.pump((0.4,))
+
+        # now there should be a SRV lookup
+        self.mock_resolver.resolve_service.assert_called_once_with(
+            b"_matrix._tcp.testserv1"
+        )
+
+        # we should fall back to a direct connection
+        self.assertEqual(len(clients), 2)
+        (host, port, client_factory, _timeout, _bindAddress) = clients[1]
+        self.assertEqual(host, '1.2.3.4')
+        self.assertEqual(port, 8448)
+
+        # make a test server, and wire up the client
+        http_server = self._make_connection(client_factory, expected_sni=b'testserv1')
+
+        # there should be no requests
+        self.assertEqual(len(http_server.requests), 0)
+
+        # ... and the request should have failed
+        e = self.failureResultOf(test_d, ResponseNeverReceived)
+        failure_reason = e.value.reasons[0]
+        self.assertIsInstance(failure_reason.value, VerificationError)
+
+    def test_get_ip_address_bad_cert(self):
+        """
+        Test the behaviour when the server name contains an explicit IP, but
+        the server cert doesn't cover it
+        """
+        # there will be a getaddrinfo on the IP
+        self.reactor.lookups["1.2.3.5"] = "1.2.3.5"
+
+        test_d = self._make_get_request(b"matrix://1.2.3.5/foo/bar")
+
+        # Nothing happened yet
+        self.assertNoResult(test_d)
+
+        # Make sure treq is trying to connect
+        clients = self.reactor.tcpClients
+        self.assertEqual(len(clients), 1)
+        (host, port, client_factory, _timeout, _bindAddress) = clients[0]
+        self.assertEqual(host, '1.2.3.5')
+        self.assertEqual(port, 8448)
+
+        # make a test server, and wire up the client
+        http_server = self._make_connection(client_factory, expected_sni=None)
+
+        # there should be no requests
+        self.assertEqual(len(http_server.requests), 0)
+
+        # ... and the request should have failed
+        e = self.failureResultOf(test_d, ResponseNeverReceived)
+        failure_reason = e.value.reasons[0]
+        self.assertIsInstance(failure_reason.value, VerificationError)
+
     def test_get_no_srv_no_well_known(self):
         """
         Test the behaviour when the server name has no port, no SRV, and no well-known
@@ -585,6 +684,49 @@ class MatrixFederationAgentTests(TestCase):
         self.reactor.pump((0.1,))
         self.successResultOf(test_d)
 
+    def test_get_well_known_unsigned_cert(self):
+        """Test the behaviour when the .well-known server presents a cert
+        not signed by a CA
+        """
+
+        # we use the same test server as the other tests, but use an agent
+        # with _well_known_tls_policy left to the default, which will not
+        # trust it (since the presented cert is signed by a test CA)
+
+        self.mock_resolver.resolve_service.side_effect = lambda _: []
+        self.reactor.lookups["testserv"] = "1.2.3.4"
+
+        agent = MatrixFederationAgent(
+            reactor=self.reactor,
+            tls_client_options_factory=ClientTLSOptionsFactory(self._config),
+            _srv_resolver=self.mock_resolver,
+            _well_known_cache=self.well_known_cache,
+        )
+
+        test_d = agent.request(b"GET", b"matrix://testserv/foo/bar")
+
+        # Nothing happened yet
+        self.assertNoResult(test_d)
+
+        # there should be an attempt to connect on port 443 for the .well-known
+        clients = self.reactor.tcpClients
+        self.assertEqual(len(clients), 1)
+        (host, port, client_factory, _timeout, _bindAddress) = clients[0]
+        self.assertEqual(host, '1.2.3.4')
+        self.assertEqual(port, 443)
+
+        http_proto = self._make_connection(
+            client_factory, expected_sni=b"testserv",
+        )
+
+        # there should be no requests
+        self.assertEqual(len(http_proto.requests), 0)
+
+        # and there should be a SRV lookup instead
+        self.mock_resolver.resolve_service.assert_called_once_with(
+            b"_matrix._tcp.testserv"
+        )
+
     def test_get_hostname_srv(self):
         """
         Test the behaviour when there is a single SRV record
@@ -918,11 +1060,17 @@ def _check_logcontext(context):
         raise AssertionError("Expected logcontext %s but was %s" % (context, current))
 
 
-def _build_test_server():
+def _build_test_server(connection_creator):
     """Construct a test server
 
     This builds an HTTP channel, wrapped with a TLSMemoryBIOProtocol
 
+    Args:
+        connection_creator (IOpenSSLServerConnectionCreator): thing to build
+            SSL connections
+        sanlist (list[bytes]): list of the SAN entries for the cert returned
+            by the server
+
     Returns:
         TLSMemoryBIOProtocol
     """
@@ -931,7 +1079,7 @@ def _build_test_server():
     server_factory.log = _log_request
 
     server_tls_factory = TLSMemoryBIOFactory(
-        ServerTLSContext(), isClient=False, wrappedFactory=server_factory
+        connection_creator, isClient=False, wrappedFactory=server_factory
     )
 
     return server_tls_factory.buildProtocol(None)
@@ -944,7 +1092,8 @@ def _log_request(request):
 
 @implementer(IPolicyForHTTPS)
 class TrustingTLSPolicyForHTTPS(object):
-    """An IPolicyForHTTPS which doesn't do any certificate verification"""
+    """An IPolicyForHTTPS which checks that the certificate belongs to the
+    right server, but doesn't check the certificate chain."""
 
     def creatorForNetloc(self, hostname, port):
         certificateOptions = OpenSSLCertificateOptions()
diff --git a/tests/http/server.key b/tests/http/server.key
new file mode 100644
index 0000000000..c53ee02b21
--- /dev/null
+++ b/tests/http/server.key
@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEpAIBAAKCAQEAvUAWLOE6TEp3FYSfEnJMwYtJg3KIW5BjiAOOvFVOVQfJ5eEa
+vzyJ1Z+8DUgLznFnUkAeD9GjPvP7awl3NPJKLQSMkV5Tp+ea4YyV+Aa4R7flROEa
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+7xEFSMIIxtpZIWSLZIFJEsCakpHBkPX4iwIveZfmt/JrM1JFTWK6ZZVGyh/BmOIZ
+Bg4lU1oBqJTUo+aZQtTCJS29b2n5OPpkNYkXTdP4e9UsVKNDvfPlYZJneUeEzxDr
+bqCPIRECgYA544KMwrWxDQZg1dsKWgdVVKx80wEFZAiQr9+0KF6ch6Iu7lwGJHFY
+iI6O85paX41qeC/Fo+feIWJVJU2GvG6eBsbO4bmq+KSg4NkABJSYxodgBp9ftNeD
+jo1tfw+gudlNe5jXHu7oSX93tqGjR4Cnlgan/KtfkB96yHOumGmOhQ==
+-----END RSA PRIVATE KEY-----
diff --git a/tests/http/server.pem b/tests/http/server.pem
deleted file mode 100644
index 0584cf1a80..0000000000
--- a/tests/http/server.pem
+++ /dev/null
@@ -1,81 +0,0 @@
------BEGIN PRIVATE KEY-----
-MIIJQgIBADANBgkqhkiG9w0BAQEFAASCCSwwggkoAgEAAoICAQCgF43/3lAgJ+p0
-x7Rn8UcL8a4fctvdkikvZrCngw96LkB34Evfq8YGWlOVjU+f9naUJLAKMatmAfEN
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-qqHh/BqNWtjxB4VZTp/g4RbgQVInZ2ozdXEv0v/dt0UEk29ANAjsZif7F3RayJ2f
-/0TilzCaJ/9K9pKNhaClVRy7Dt8QjYg6BIWCGSw4ApF7pLnQ9gySn95mersCkVzD
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-/q7Ee8hem1Rn5RFHu14FV45RS4LAWl6wvf5pQtneSKzx8YL0GZIRRytOzdEfnGKr
-FeUlAj5uL+5/p0ZEgM7gPsEBwdm8scF79qSUn8UWSoXNeIauF9D4BDg8RZcFFxka
-KILVFsq3cQC+bEnoM4eVbjEQkGs1RQ==
------END PRIVATE KEY-----
------BEGIN CERTIFICATE-----
-MIIE/jCCAuagAwIBAgIJANFtVaGvJWZlMA0GCSqGSIb3DQEBCwUAMBMxETAPBgNV
-BAMMCHRlc3RzZXJ2MCAXDTE5MDEyNzIyMDIzNloYDzIxMTkwMTAzMjIwMjM2WjAT
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-f0ytW6qZ0TpHbD6gOtQLYDnhx3ISuX+QYSekVwQUpffeWQ==
------END CERTIFICATE-----