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-rw-r--r--tests/config/test_server.py8
-rw-r--r--tests/handlers/test_room.py108
-rw-r--r--tests/handlers/test_room_summary.py43
-rw-r--r--tests/handlers/test_user_directory.py96
-rw-r--r--tests/push/test_email.py52
-rw-r--r--tests/rest/media/v1/test_url_preview.py212
-rw-r--r--tests/storage/databases/main/test_room.py98
7 files changed, 398 insertions, 219 deletions
diff --git a/tests/config/test_server.py b/tests/config/test_server.py
index 6f2b9e997d..b6f21294ba 100644
--- a/tests/config/test_server.py
+++ b/tests/config/test_server.py
@@ -35,7 +35,7 @@ class ServerConfigTestCase(unittest.TestCase):
     def test_unsecure_listener_no_listeners_open_private_ports_false(self):
         conf = yaml.safe_load(
             ServerConfig().generate_config_section(
-                "che.org", "/data_dir_path", False, None
+                "che.org", "/data_dir_path", False, None, config_dir_path="CONFDIR"
             )
         )
 
@@ -55,7 +55,7 @@ class ServerConfigTestCase(unittest.TestCase):
     def test_unsecure_listener_no_listeners_open_private_ports_true(self):
         conf = yaml.safe_load(
             ServerConfig().generate_config_section(
-                "che.org", "/data_dir_path", True, None
+                "che.org", "/data_dir_path", True, None, config_dir_path="CONFDIR"
             )
         )
 
@@ -89,7 +89,7 @@ class ServerConfigTestCase(unittest.TestCase):
 
         conf = yaml.safe_load(
             ServerConfig().generate_config_section(
-                "this.one.listens", "/data_dir_path", True, listeners
+                "this.one.listens", "/data_dir_path", True, listeners, "CONFDIR"
             )
         )
 
@@ -123,7 +123,7 @@ class ServerConfigTestCase(unittest.TestCase):
 
         conf = yaml.safe_load(
             ServerConfig().generate_config_section(
-                "this.one.listens", "/data_dir_path", True, listeners
+                "this.one.listens", "/data_dir_path", True, listeners, "CONFDIR"
             )
         )
 
diff --git a/tests/handlers/test_room.py b/tests/handlers/test_room.py
new file mode 100644
index 0000000000..fcde5dab72
--- /dev/null
+++ b/tests/handlers/test_room.py
@@ -0,0 +1,108 @@
+import synapse
+from synapse.api.constants import EventTypes, RoomEncryptionAlgorithms
+from synapse.rest.client import login, room
+
+from tests import unittest
+from tests.unittest import override_config
+
+
+class EncryptedByDefaultTestCase(unittest.HomeserverTestCase):
+    servlets = [
+        login.register_servlets,
+        synapse.rest.admin.register_servlets_for_client_rest_resource,
+        room.register_servlets,
+    ]
+
+    @override_config({"encryption_enabled_by_default_for_room_type": "all"})
+    def test_encrypted_by_default_config_option_all(self):
+        """Tests that invite-only and non-invite-only rooms have encryption enabled by
+        default when the config option encryption_enabled_by_default_for_room_type is "all".
+        """
+        # Create a user
+        user = self.register_user("user", "pass")
+        user_token = self.login(user, "pass")
+
+        # Create an invite-only room as that user
+        room_id = self.helper.create_room_as(user, is_public=False, tok=user_token)
+
+        # Check that the room has an encryption state event
+        event_content = self.helper.get_state(
+            room_id=room_id,
+            event_type=EventTypes.RoomEncryption,
+            tok=user_token,
+        )
+        self.assertEqual(event_content, {"algorithm": RoomEncryptionAlgorithms.DEFAULT})
+
+        # Create a non invite-only room as that user
+        room_id = self.helper.create_room_as(user, is_public=True, tok=user_token)
+
+        # Check that the room has an encryption state event
+        event_content = self.helper.get_state(
+            room_id=room_id,
+            event_type=EventTypes.RoomEncryption,
+            tok=user_token,
+        )
+        self.assertEqual(event_content, {"algorithm": RoomEncryptionAlgorithms.DEFAULT})
+
+    @override_config({"encryption_enabled_by_default_for_room_type": "invite"})
+    def test_encrypted_by_default_config_option_invite(self):
+        """Tests that only new, invite-only rooms have encryption enabled by default when
+        the config option encryption_enabled_by_default_for_room_type is "invite".
+        """
+        # Create a user
+        user = self.register_user("user", "pass")
+        user_token = self.login(user, "pass")
+
+        # Create an invite-only room as that user
+        room_id = self.helper.create_room_as(user, is_public=False, tok=user_token)
+
+        # Check that the room has an encryption state event
+        event_content = self.helper.get_state(
+            room_id=room_id,
+            event_type=EventTypes.RoomEncryption,
+            tok=user_token,
+        )
+        self.assertEqual(event_content, {"algorithm": RoomEncryptionAlgorithms.DEFAULT})
+
+        # Create a non invite-only room as that user
+        room_id = self.helper.create_room_as(user, is_public=True, tok=user_token)
+
+        # Check that the room does not have an encryption state event
+        self.helper.get_state(
+            room_id=room_id,
+            event_type=EventTypes.RoomEncryption,
+            tok=user_token,
+            expect_code=404,
+        )
+
+    @override_config({"encryption_enabled_by_default_for_room_type": "off"})
+    def test_encrypted_by_default_config_option_off(self):
+        """Tests that neither new invite-only nor non-invite-only rooms have encryption
+        enabled by default when the config option
+        encryption_enabled_by_default_for_room_type is "off".
+        """
+        # Create a user
+        user = self.register_user("user", "pass")
+        user_token = self.login(user, "pass")
+
+        # Create an invite-only room as that user
+        room_id = self.helper.create_room_as(user, is_public=False, tok=user_token)
+
+        # Check that the room does not have an encryption state event
+        self.helper.get_state(
+            room_id=room_id,
+            event_type=EventTypes.RoomEncryption,
+            tok=user_token,
+            expect_code=404,
+        )
+
+        # Create a non invite-only room as that user
+        room_id = self.helper.create_room_as(user, is_public=True, tok=user_token)
+
+        # Check that the room does not have an encryption state event
+        self.helper.get_state(
+            room_id=room_id,
+            event_type=EventTypes.RoomEncryption,
+            tok=user_token,
+            expect_code=404,
+        )
diff --git a/tests/handlers/test_room_summary.py b/tests/handlers/test_room_summary.py
index ac800afa7d..d3d0bf1ac5 100644
--- a/tests/handlers/test_room_summary.py
+++ b/tests/handlers/test_room_summary.py
@@ -35,10 +35,11 @@ from synapse.types import JsonDict, UserID
 from tests import unittest
 
 
-def _create_event(room_id: str, order: Optional[Any] = None):
-    result = mock.Mock()
+def _create_event(room_id: str, order: Optional[Any] = None, origin_server_ts: int = 0):
+    result = mock.Mock(name=room_id)
     result.room_id = room_id
     result.content = {}
+    result.origin_server_ts = origin_server_ts
     if order is not None:
         result.content["order"] = order
     return result
@@ -63,10 +64,17 @@ class TestSpaceSummarySort(unittest.TestCase):
 
         self.assertEqual([ev2, ev1], _order(ev1, ev2))
 
+    def test_order_origin_server_ts(self):
+        """Origin server  is a tie-breaker for ordering."""
+        ev1 = _create_event("!abc:test", origin_server_ts=10)
+        ev2 = _create_event("!xyz:test", origin_server_ts=30)
+
+        self.assertEqual([ev1, ev2], _order(ev1, ev2))
+
     def test_order_room_id(self):
-        """Room ID is a tie-breaker for ordering."""
-        ev1 = _create_event("!abc:test", "abc")
-        ev2 = _create_event("!xyz:test", "abc")
+        """Room ID is a final tie-breaker for ordering."""
+        ev1 = _create_event("!abc:test")
+        ev2 = _create_event("!xyz:test")
 
         self.assertEqual([ev1, ev2], _order(ev1, ev2))
 
@@ -573,6 +581,31 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
         ]
         self._assert_hierarchy(result, expected)
 
+    def test_unknown_room_version(self):
+        """
+        If an room with an unknown room version is encountered it should not cause
+        the entire summary to skip.
+        """
+        # Poke the database and update the room version to an unknown one.
+        self.get_success(
+            self.hs.get_datastores().main.db_pool.simple_update(
+                "rooms",
+                keyvalues={"room_id": self.room},
+                updatevalues={"room_version": "unknown-room-version"},
+                desc="updated-room-version",
+            )
+        )
+
+        result = self.get_success(self.handler.get_space_summary(self.user, self.space))
+        # The result should have only the space, along with a link from space -> room.
+        expected = [(self.space, [self.room])]
+        self._assert_rooms(result, expected)
+
+        result = self.get_success(
+            self.handler.get_room_hierarchy(self.user, self.space)
+        )
+        self._assert_hierarchy(result, expected)
+
     def test_fed_complex(self):
         """
         Return data over federation and ensure that it is handled properly.
diff --git a/tests/handlers/test_user_directory.py b/tests/handlers/test_user_directory.py
index e44bf2b3b1..a91d31ce61 100644
--- a/tests/handlers/test_user_directory.py
+++ b/tests/handlers/test_user_directory.py
@@ -16,7 +16,7 @@ from unittest.mock import Mock
 from twisted.internet import defer
 
 import synapse.rest.admin
-from synapse.api.constants import EventTypes, RoomEncryptionAlgorithms, UserTypes
+from synapse.api.constants import UserTypes
 from synapse.api.room_versions import RoomVersion, RoomVersions
 from synapse.rest.client import login, room, user_directory
 from synapse.storage.roommember import ProfileInfo
@@ -187,100 +187,6 @@ class UserDirectoryTestCase(unittest.HomeserverTestCase):
         s = self.get_success(self.handler.search_users(u1, "user3", 10))
         self.assertEqual(len(s["results"]), 0)
 
-    @override_config({"encryption_enabled_by_default_for_room_type": "all"})
-    def test_encrypted_by_default_config_option_all(self):
-        """Tests that invite-only and non-invite-only rooms have encryption enabled by
-        default when the config option encryption_enabled_by_default_for_room_type is "all".
-        """
-        # Create a user
-        user = self.register_user("user", "pass")
-        user_token = self.login(user, "pass")
-
-        # Create an invite-only room as that user
-        room_id = self.helper.create_room_as(user, is_public=False, tok=user_token)
-
-        # Check that the room has an encryption state event
-        event_content = self.helper.get_state(
-            room_id=room_id,
-            event_type=EventTypes.RoomEncryption,
-            tok=user_token,
-        )
-        self.assertEqual(event_content, {"algorithm": RoomEncryptionAlgorithms.DEFAULT})
-
-        # Create a non invite-only room as that user
-        room_id = self.helper.create_room_as(user, is_public=True, tok=user_token)
-
-        # Check that the room has an encryption state event
-        event_content = self.helper.get_state(
-            room_id=room_id,
-            event_type=EventTypes.RoomEncryption,
-            tok=user_token,
-        )
-        self.assertEqual(event_content, {"algorithm": RoomEncryptionAlgorithms.DEFAULT})
-
-    @override_config({"encryption_enabled_by_default_for_room_type": "invite"})
-    def test_encrypted_by_default_config_option_invite(self):
-        """Tests that only new, invite-only rooms have encryption enabled by default when
-        the config option encryption_enabled_by_default_for_room_type is "invite".
-        """
-        # Create a user
-        user = self.register_user("user", "pass")
-        user_token = self.login(user, "pass")
-
-        # Create an invite-only room as that user
-        room_id = self.helper.create_room_as(user, is_public=False, tok=user_token)
-
-        # Check that the room has an encryption state event
-        event_content = self.helper.get_state(
-            room_id=room_id,
-            event_type=EventTypes.RoomEncryption,
-            tok=user_token,
-        )
-        self.assertEqual(event_content, {"algorithm": RoomEncryptionAlgorithms.DEFAULT})
-
-        # Create a non invite-only room as that user
-        room_id = self.helper.create_room_as(user, is_public=True, tok=user_token)
-
-        # Check that the room does not have an encryption state event
-        self.helper.get_state(
-            room_id=room_id,
-            event_type=EventTypes.RoomEncryption,
-            tok=user_token,
-            expect_code=404,
-        )
-
-    @override_config({"encryption_enabled_by_default_for_room_type": "off"})
-    def test_encrypted_by_default_config_option_off(self):
-        """Tests that neither new invite-only nor non-invite-only rooms have encryption
-        enabled by default when the config option
-        encryption_enabled_by_default_for_room_type is "off".
-        """
-        # Create a user
-        user = self.register_user("user", "pass")
-        user_token = self.login(user, "pass")
-
-        # Create an invite-only room as that user
-        room_id = self.helper.create_room_as(user, is_public=False, tok=user_token)
-
-        # Check that the room does not have an encryption state event
-        self.helper.get_state(
-            room_id=room_id,
-            event_type=EventTypes.RoomEncryption,
-            tok=user_token,
-            expect_code=404,
-        )
-
-        # Create a non invite-only room as that user
-        room_id = self.helper.create_room_as(user, is_public=True, tok=user_token)
-
-        # Check that the room does not have an encryption state event
-        self.helper.get_state(
-            room_id=room_id,
-            event_type=EventTypes.RoomEncryption,
-            tok=user_token,
-            expect_code=404,
-        )
-
     def test_spam_checker(self):
         """
         A user which fails the spam checks will not appear in search results.
diff --git a/tests/push/test_email.py b/tests/push/test_email.py
index c4ba13a6b2..fa8018e5a7 100644
--- a/tests/push/test_email.py
+++ b/tests/push/test_email.py
@@ -11,8 +11,9 @@
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
 # limitations under the License.
-
+import email.message
 import os
+from typing import Dict, List, Sequence, Tuple
 
 import attr
 import pkg_resources
@@ -70,9 +71,10 @@ class EmailPusherTests(HomeserverTestCase):
         hs = self.setup_test_homeserver(config=config)
 
         # List[Tuple[Deferred, args, kwargs]]
-        self.email_attempts = []
+        self.email_attempts: List[Tuple[Deferred, Sequence, Dict]] = []
 
         def sendmail(*args, **kwargs):
+            # This mocks out synapse.reactor.send_email._sendmail.
             d = Deferred()
             self.email_attempts.append((d, args, kwargs))
             return d
@@ -255,6 +257,39 @@ class EmailPusherTests(HomeserverTestCase):
         # We should get emailed about those messages
         self._check_for_mail()
 
+    def test_room_notifications_include_avatar(self):
+        # Create a room and set its avatar.
+        room = self.helper.create_room_as(self.user_id, tok=self.access_token)
+        self.helper.send_state(
+            room, "m.room.avatar", {"url": "mxc://DUMMY_MEDIA_ID"}, self.access_token
+        )
+
+        # Invite two other uses.
+        for other in self.others:
+            self.helper.invite(
+                room=room, src=self.user_id, tok=self.access_token, targ=other.id
+            )
+            self.helper.join(room=room, user=other.id, tok=other.token)
+
+        # The other users send some messages.
+        # TODO It seems that two messages are required to trigger an email?
+        self.helper.send(room, body="Alpha", tok=self.others[0].token)
+        self.helper.send(room, body="Beta", tok=self.others[1].token)
+
+        # We should get emailed about those messages
+        args, kwargs = self._check_for_mail()
+
+        # That email should contain the room's avatar
+        msg: bytes = args[5]
+        # Multipart: plain text, base 64 encoded; html, base 64 encoded
+        html = (
+            email.message_from_bytes(msg)
+            .get_payload()[1]
+            .get_payload(decode=True)
+            .decode()
+        )
+        self.assertIn("_matrix/media/v1/thumbnail/DUMMY_MEDIA_ID", html)
+
     def test_empty_room(self):
         """All users leaving a room shouldn't cause the pusher to break."""
         # Create a simple room with two users
@@ -388,9 +423,14 @@ class EmailPusherTests(HomeserverTestCase):
         pushers = list(pushers)
         self.assertEqual(len(pushers), 0)
 
-    def _check_for_mail(self):
-        """Check that the user receives an email notification"""
+    def _check_for_mail(self) -> Tuple[Sequence, Dict]:
+        """
+        Assert that synapse sent off exactly one email notification.
 
+        Returns:
+            args and kwargs passed to synapse.reactor.send_email._sendmail for
+            that notification.
+        """
         # Get the stream ordering before it gets sent
         pushers = self.get_success(
             self.hs.get_datastore().get_pushers_by({"user_name": self.user_id})
@@ -413,8 +453,9 @@ class EmailPusherTests(HomeserverTestCase):
         # One email was attempted to be sent
         self.assertEqual(len(self.email_attempts), 1)
 
+        deferred, sendmail_args, sendmail_kwargs = self.email_attempts[0]
         # Make the email succeed
-        self.email_attempts[0][0].callback(True)
+        deferred.callback(True)
         self.pump()
 
         # One email was attempted to be sent
@@ -430,3 +471,4 @@ class EmailPusherTests(HomeserverTestCase):
 
         # Reset the attempts.
         self.email_attempts = []
+        return sendmail_args, sendmail_kwargs
diff --git a/tests/rest/media/v1/test_url_preview.py b/tests/rest/media/v1/test_url_preview.py
index d3ef7bb4c6..7fa9027227 100644
--- a/tests/rest/media/v1/test_url_preview.py
+++ b/tests/rest/media/v1/test_url_preview.py
@@ -14,13 +14,14 @@
 import json
 import os
 import re
-from unittest.mock import patch
 
 from twisted.internet._resolver import HostResolution
 from twisted.internet.address import IPv4Address, IPv6Address
 from twisted.internet.error import DNSLookupError
 from twisted.test.proto_helpers import AccumulatingProtocol
 
+from synapse.config.oembed import OEmbedEndpointConfig
+
 from tests import unittest
 from tests.server import FakeTransport
 
@@ -81,6 +82,19 @@ class URLPreviewTests(unittest.HomeserverTestCase):
 
         hs = self.setup_test_homeserver(config=config)
 
+        # After the hs is created, modify the parsed oEmbed config (to avoid
+        # messing with files).
+        #
+        # Note that HTTP URLs are used to avoid having to deal with TLS in tests.
+        hs.config.oembed.oembed_patterns = [
+            OEmbedEndpointConfig(
+                api_endpoint="http://publish.twitter.com/oembed",
+                url_patterns=[
+                    re.compile(r"http://twitter\.com/.+/status/.+"),
+                ],
+            )
+        ]
+
         return hs
 
     def prepare(self, reactor, clock, hs):
@@ -544,123 +558,101 @@ class URLPreviewTests(unittest.HomeserverTestCase):
 
     def test_oembed_photo(self):
         """Test an oEmbed endpoint which returns a 'photo' type which redirects the preview to a new URL."""
-        # Route the HTTP version to an HTTP endpoint so that the tests work.
-        with patch.dict(
-            "synapse.rest.media.v1.preview_url_resource._oembed_patterns",
-            {
-                re.compile(
-                    r"http://twitter\.com/.+/status/.+"
-                ): "http://publish.twitter.com/oembed",
-            },
-            clear=True,
-        ):
-
-            self.lookups["publish.twitter.com"] = [(IPv4Address, "10.1.2.3")]
-            self.lookups["cdn.twitter.com"] = [(IPv4Address, "10.1.2.3")]
-
-            result = {
-                "version": "1.0",
-                "type": "photo",
-                "url": "http://cdn.twitter.com/matrixdotorg",
-            }
-            oembed_content = json.dumps(result).encode("utf-8")
-
-            end_content = (
-                b"<html><head>"
-                b"<title>Some Title</title>"
-                b'<meta property="og:description" content="hi" />'
-                b"</head></html>"
-            )
+        self.lookups["publish.twitter.com"] = [(IPv4Address, "10.1.2.3")]
+        self.lookups["cdn.twitter.com"] = [(IPv4Address, "10.1.2.3")]
 
-            channel = self.make_request(
-                "GET",
-                "preview_url?url=http://twitter.com/matrixdotorg/status/12345",
-                shorthand=False,
-                await_result=False,
-            )
-            self.pump()
-
-            client = self.reactor.tcpClients[0][2].buildProtocol(None)
-            server = AccumulatingProtocol()
-            server.makeConnection(FakeTransport(client, self.reactor))
-            client.makeConnection(FakeTransport(server, self.reactor))
-            client.dataReceived(
-                (
-                    b"HTTP/1.0 200 OK\r\nContent-Length: %d\r\n"
-                    b'Content-Type: application/json; charset="utf8"\r\n\r\n'
-                )
-                % (len(oembed_content),)
-                + oembed_content
-            )
+        result = {
+            "version": "1.0",
+            "type": "photo",
+            "url": "http://cdn.twitter.com/matrixdotorg",
+        }
+        oembed_content = json.dumps(result).encode("utf-8")
 
-            self.pump()
-
-            client = self.reactor.tcpClients[1][2].buildProtocol(None)
-            server = AccumulatingProtocol()
-            server.makeConnection(FakeTransport(client, self.reactor))
-            client.makeConnection(FakeTransport(server, self.reactor))
-            client.dataReceived(
-                (
-                    b"HTTP/1.0 200 OK\r\nContent-Length: %d\r\n"
-                    b'Content-Type: text/html; charset="utf8"\r\n\r\n'
-                )
-                % (len(end_content),)
-                + end_content
+        end_content = (
+            b"<html><head>"
+            b"<title>Some Title</title>"
+            b'<meta property="og:description" content="hi" />'
+            b"</head></html>"
+        )
+
+        channel = self.make_request(
+            "GET",
+            "preview_url?url=http://twitter.com/matrixdotorg/status/12345",
+            shorthand=False,
+            await_result=False,
+        )
+        self.pump()
+
+        client = self.reactor.tcpClients[0][2].buildProtocol(None)
+        server = AccumulatingProtocol()
+        server.makeConnection(FakeTransport(client, self.reactor))
+        client.makeConnection(FakeTransport(server, self.reactor))
+        client.dataReceived(
+            (
+                b"HTTP/1.0 200 OK\r\nContent-Length: %d\r\n"
+                b'Content-Type: application/json; charset="utf8"\r\n\r\n'
             )
+            % (len(oembed_content),)
+            + oembed_content
+        )
 
-            self.pump()
+        self.pump()
 
-            self.assertEqual(channel.code, 200)
-            self.assertEqual(
-                channel.json_body, {"og:title": "Some Title", "og:description": "hi"}
+        client = self.reactor.tcpClients[1][2].buildProtocol(None)
+        server = AccumulatingProtocol()
+        server.makeConnection(FakeTransport(client, self.reactor))
+        client.makeConnection(FakeTransport(server, self.reactor))
+        client.dataReceived(
+            (
+                b"HTTP/1.0 200 OK\r\nContent-Length: %d\r\n"
+                b'Content-Type: text/html; charset="utf8"\r\n\r\n'
             )
+            % (len(end_content),)
+            + end_content
+        )
+
+        self.pump()
+
+        self.assertEqual(channel.code, 200)
+        self.assertEqual(
+            channel.json_body, {"og:title": "Some Title", "og:description": "hi"}
+        )
 
     def test_oembed_rich(self):
         """Test an oEmbed endpoint which returns HTML content via the 'rich' type."""
-        # Route the HTTP version to an HTTP endpoint so that the tests work.
-        with patch.dict(
-            "synapse.rest.media.v1.preview_url_resource._oembed_patterns",
-            {
-                re.compile(
-                    r"http://twitter\.com/.+/status/.+"
-                ): "http://publish.twitter.com/oembed",
-            },
-            clear=True,
-        ):
-
-            self.lookups["publish.twitter.com"] = [(IPv4Address, "10.1.2.3")]
-
-            result = {
-                "version": "1.0",
-                "type": "rich",
-                "html": "<div>Content Preview</div>",
-            }
-            end_content = json.dumps(result).encode("utf-8")
-
-            channel = self.make_request(
-                "GET",
-                "preview_url?url=http://twitter.com/matrixdotorg/status/12345",
-                shorthand=False,
-                await_result=False,
-            )
-            self.pump()
-
-            client = self.reactor.tcpClients[0][2].buildProtocol(None)
-            server = AccumulatingProtocol()
-            server.makeConnection(FakeTransport(client, self.reactor))
-            client.makeConnection(FakeTransport(server, self.reactor))
-            client.dataReceived(
-                (
-                    b"HTTP/1.0 200 OK\r\nContent-Length: %d\r\n"
-                    b'Content-Type: application/json; charset="utf8"\r\n\r\n'
-                )
-                % (len(end_content),)
-                + end_content
-            )
+        self.lookups["publish.twitter.com"] = [(IPv4Address, "10.1.2.3")]
+
+        result = {
+            "version": "1.0",
+            "type": "rich",
+            "html": "<div>Content Preview</div>",
+        }
+        end_content = json.dumps(result).encode("utf-8")
+
+        channel = self.make_request(
+            "GET",
+            "preview_url?url=http://twitter.com/matrixdotorg/status/12345",
+            shorthand=False,
+            await_result=False,
+        )
+        self.pump()
 
-            self.pump()
-            self.assertEqual(channel.code, 200)
-            self.assertEqual(
-                channel.json_body,
-                {"og:title": None, "og:description": "Content Preview"},
+        client = self.reactor.tcpClients[0][2].buildProtocol(None)
+        server = AccumulatingProtocol()
+        server.makeConnection(FakeTransport(client, self.reactor))
+        client.makeConnection(FakeTransport(server, self.reactor))
+        client.dataReceived(
+            (
+                b"HTTP/1.0 200 OK\r\nContent-Length: %d\r\n"
+                b'Content-Type: application/json; charset="utf8"\r\n\r\n'
             )
+            % (len(end_content),)
+            + end_content
+        )
+
+        self.pump()
+        self.assertEqual(channel.code, 200)
+        self.assertEqual(
+            channel.json_body,
+            {"og:title": None, "og:description": "Content Preview"},
+        )
diff --git a/tests/storage/databases/main/test_room.py b/tests/storage/databases/main/test_room.py
new file mode 100644
index 0000000000..ffee707153
--- /dev/null
+++ b/tests/storage/databases/main/test_room.py
@@ -0,0 +1,98 @@
+# Copyright 2021 The Matrix.org Foundation C.I.C.
+#
+# Licensed under the Apache License, Version 2.0 (the 'License');
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an 'AS IS' BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+from synapse.rest import admin
+from synapse.rest.client import login, room
+from synapse.storage.databases.main.room import _BackgroundUpdates
+
+from tests.unittest import HomeserverTestCase
+
+
+class RoomBackgroundUpdateStoreTestCase(HomeserverTestCase):
+
+    servlets = [
+        admin.register_servlets,
+        room.register_servlets,
+        login.register_servlets,
+    ]
+
+    def prepare(self, reactor, clock, hs):
+        self.store = hs.get_datastore()
+        self.user_id = self.register_user("foo", "pass")
+        self.token = self.login("foo", "pass")
+
+    def _generate_room(self) -> str:
+        room_id = self.helper.create_room_as(self.user_id, tok=self.token)
+
+        return room_id
+
+    def test_background_populate_rooms_creator_column(self):
+        """Test that the background update to populate the rooms creator column
+        works properly.
+        """
+
+        # Insert a room without the creator
+        room_id = self._generate_room()
+        self.get_success(
+            self.store.db_pool.simple_update(
+                table="rooms",
+                keyvalues={"room_id": room_id},
+                updatevalues={"creator": None},
+                desc="test",
+            )
+        )
+
+        # Make sure the test is starting out with a room without a creator
+        room_creator_before = self.get_success(
+            self.store.db_pool.simple_select_one_onecol(
+                table="rooms",
+                keyvalues={"room_id": room_id},
+                retcol="creator",
+                allow_none=True,
+            )
+        )
+        self.assertEqual(room_creator_before, None)
+
+        # Insert and run the background update.
+        self.get_success(
+            self.store.db_pool.simple_insert(
+                "background_updates",
+                {
+                    "update_name": _BackgroundUpdates.POPULATE_ROOMS_CREATOR_COLUMN,
+                    "progress_json": "{}",
+                },
+            )
+        )
+
+        # ... and tell the DataStore that it hasn't finished all updates yet
+        self.store.db_pool.updates._all_done = False
+
+        # Now let's actually drive the updates to completion
+        while not self.get_success(
+            self.store.db_pool.updates.has_completed_background_updates()
+        ):
+            self.get_success(
+                self.store.db_pool.updates.do_next_background_update(100), by=0.1
+            )
+
+        # Make sure the background update filled in the room creator
+        room_creator_after = self.get_success(
+            self.store.db_pool.simple_select_one_onecol(
+                table="rooms",
+                keyvalues={"room_id": room_id},
+                retcol="creator",
+                allow_none=True,
+            )
+        )
+        self.assertEqual(room_creator_after, self.user_id)