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+#  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 typing import List
+
+from synapse.api.constants import EventTypes, RelationTypes
+from synapse.api.filtering import Filter
+from synapse.events import EventBase
+from synapse.rest import admin
+from synapse.rest.client import login, room
+from synapse.types import JsonDict
+
+from tests.unittest import HomeserverTestCase
+
+
+class PaginationTestCase(HomeserverTestCase):
+    """
+    Test the pre-filtering done in the pagination code.
+
+    This is similar to some of the tests in tests.rest.client.test_rooms but here
+    we ensure that the filtering done in the database is applied successfully.
+    """
+
+    servlets = [
+        admin.register_servlets_for_client_rest_resource,
+        room.register_servlets,
+        login.register_servlets,
+    ]
+
+    def default_config(self):
+        config = super().default_config()
+        config["experimental_features"] = {"msc3440_enabled": True}
+        return config
+
+    def prepare(self, reactor, clock, homeserver):
+        self.user_id = self.register_user("test", "test")
+        self.tok = self.login("test", "test")
+        self.room_id = self.helper.create_room_as(self.user_id, tok=self.tok)
+
+        self.second_user_id = self.register_user("second", "test")
+        self.second_tok = self.login("second", "test")
+        self.helper.join(
+            room=self.room_id, user=self.second_user_id, tok=self.second_tok
+        )
+
+        self.third_user_id = self.register_user("third", "test")
+        self.third_tok = self.login("third", "test")
+        self.helper.join(room=self.room_id, user=self.third_user_id, tok=self.third_tok)
+
+        # An initial event with a relation from second user.
+        res = self.helper.send_event(
+            room_id=self.room_id,
+            type=EventTypes.Message,
+            content={"msgtype": "m.text", "body": "Message 1"},
+            tok=self.tok,
+        )
+        self.event_id_1 = res["event_id"]
+        self.helper.send_event(
+            room_id=self.room_id,
+            type="m.reaction",
+            content={
+                "m.relates_to": {
+                    "rel_type": RelationTypes.ANNOTATION,
+                    "event_id": self.event_id_1,
+                    "key": "👍",
+                }
+            },
+            tok=self.second_tok,
+        )
+
+        # Another event with a relation from third user.
+        res = self.helper.send_event(
+            room_id=self.room_id,
+            type=EventTypes.Message,
+            content={"msgtype": "m.text", "body": "Message 2"},
+            tok=self.tok,
+        )
+        self.event_id_2 = res["event_id"]
+        self.helper.send_event(
+            room_id=self.room_id,
+            type="m.reaction",
+            content={
+                "m.relates_to": {
+                    "rel_type": RelationTypes.REFERENCE,
+                    "event_id": self.event_id_2,
+                }
+            },
+            tok=self.third_tok,
+        )
+
+        # An event with no relations.
+        self.helper.send_event(
+            room_id=self.room_id,
+            type=EventTypes.Message,
+            content={"msgtype": "m.text", "body": "No relations"},
+            tok=self.tok,
+        )
+
+    def _filter_messages(self, filter: JsonDict) -> List[EventBase]:
+        """Make a request to /messages with a filter, returns the chunk of events."""
+
+        from_token = self.get_success(
+            self.hs.get_event_sources().get_current_token_for_pagination()
+        )
+
+        events, next_key = self.get_success(
+            self.hs.get_datastore().paginate_room_events(
+                room_id=self.room_id,
+                from_key=from_token.room_key,
+                to_key=None,
+                direction="b",
+                limit=10,
+                event_filter=Filter(self.hs, filter),
+            )
+        )
+
+        return events
+
+    def test_filter_relation_senders(self):
+        # Messages which second user reacted to.
+        filter = {"io.element.relation_senders": [self.second_user_id]}
+        chunk = self._filter_messages(filter)
+        self.assertEqual(len(chunk), 1, chunk)
+        self.assertEqual(chunk[0].event_id, self.event_id_1)
+
+        # Messages which third user reacted to.
+        filter = {"io.element.relation_senders": [self.third_user_id]}
+        chunk = self._filter_messages(filter)
+        self.assertEqual(len(chunk), 1, chunk)
+        self.assertEqual(chunk[0].event_id, self.event_id_2)
+
+        # Messages which either user reacted to.
+        filter = {
+            "io.element.relation_senders": [self.second_user_id, self.third_user_id]
+        }
+        chunk = self._filter_messages(filter)
+        self.assertEqual(len(chunk), 2, chunk)
+        self.assertCountEqual(
+            [c.event_id for c in chunk], [self.event_id_1, self.event_id_2]
+        )
+
+    def test_filter_relation_type(self):
+        # Messages which have annotations.
+        filter = {"io.element.relation_types": [RelationTypes.ANNOTATION]}
+        chunk = self._filter_messages(filter)
+        self.assertEqual(len(chunk), 1, chunk)
+        self.assertEqual(chunk[0].event_id, self.event_id_1)
+
+        # Messages which have references.
+        filter = {"io.element.relation_types": [RelationTypes.REFERENCE]}
+        chunk = self._filter_messages(filter)
+        self.assertEqual(len(chunk), 1, chunk)
+        self.assertEqual(chunk[0].event_id, self.event_id_2)
+
+        # Messages which have either annotations or references.
+        filter = {
+            "io.element.relation_types": [
+                RelationTypes.ANNOTATION,
+                RelationTypes.REFERENCE,
+            ]
+        }
+        chunk = self._filter_messages(filter)
+        self.assertEqual(len(chunk), 2, chunk)
+        self.assertCountEqual(
+            [c.event_id for c in chunk], [self.event_id_1, self.event_id_2]
+        )
+
+    def test_filter_relation_senders_and_type(self):
+        # Messages which second user reacted to.
+        filter = {
+            "io.element.relation_senders": [self.second_user_id],
+            "io.element.relation_types": [RelationTypes.ANNOTATION],
+        }
+        chunk = self._filter_messages(filter)
+        self.assertEqual(len(chunk), 1, chunk)
+        self.assertEqual(chunk[0].event_id, self.event_id_1)
+
+    def test_duplicate_relation(self):
+        """An event should only be returned once if there are multiple relations to it."""
+        self.helper.send_event(
+            room_id=self.room_id,
+            type="m.reaction",
+            content={
+                "m.relates_to": {
+                    "rel_type": RelationTypes.ANNOTATION,
+                    "event_id": self.event_id_1,
+                    "key": "A",
+                }
+            },
+            tok=self.second_tok,
+        )
+
+        filter = {"io.element.relation_senders": [self.second_user_id]}
+        chunk = self._filter_messages(filter)
+        self.assertEqual(len(chunk), 1, chunk)
+        self.assertEqual(chunk[0].event_id, self.event_id_1)