diff --git a/tests/rest/client/v1/test_rooms.py b/tests/rest/client/v1/test_rooms.py
index 5e38fd6ced..621c894e35 100644
--- a/tests/rest/client/v1/test_rooms.py
+++ b/tests/rest/client/v1/test_rooms.py
@@ -1106,3 +1106,185 @@ class PerRoomProfilesForbiddenTestCase(unittest.HomeserverTestCase):
res_displayname = channel.json_body["content"]["displayname"]
self.assertEqual(res_displayname, self.displayname, channel.result)
+
+
+class ContextTestCase(unittest.HomeserverTestCase):
+ servlets = [
+ synapse.rest.admin.register_servlets_for_client_rest_resource,
+ room.register_servlets,
+ login.register_servlets,
+ profile.register_servlets,
+ ]
+
+ def test_context_filter_labels(self):
+ """Test that we can filter by a label."""
+ context_filter = json.dumps(
+ {
+ "types": [EventTypes.Message],
+ "org.matrix.labels": ["#fun"],
+ }
+ )
+
+ res = self._test_context_filter_labels(context_filter)
+
+ self.assertEqual(
+ res["event"]["content"]["body"], "with right label", res["event"]
+ )
+
+ events_before = res["events_before"]
+
+ self.assertEqual(
+ len(events_before), 1, [event["content"] for event in events_before]
+ )
+ self.assertEqual(
+ events_before[0]["content"]["body"], "with right label", events_before[0]
+ )
+
+ events_after = res["events_before"]
+
+ self.assertEqual(
+ len(events_after), 1, [event["content"] for event in events_after]
+ )
+ self.assertEqual(
+ events_after[0]["content"]["body"], "with right label", events_after[0]
+ )
+
+ def test_context_filter_not_labels(self):
+ """Test that we can filter by the absence of a label."""
+ context_filter = json.dumps(
+ {
+ "types": [EventTypes.Message],
+ "org.matrix.not_labels": ["#fun"],
+ }
+ )
+
+ res = self._test_context_filter_labels(context_filter)
+
+ events_before = res["events_before"]
+
+ self.assertEqual(
+ len(events_before), 1, [event["content"] for event in events_before]
+ )
+ self.assertEqual(
+ events_before[0]["content"]["body"], "without label", events_before[0]
+ )
+
+ events_after = res["events_after"]
+
+ self.assertEqual(
+ len(events_after), 2, [event["content"] for event in events_after]
+ )
+ self.assertEqual(
+ events_after[0]["content"]["body"], "with wrong label", events_after[0]
+ )
+ self.assertEqual(
+ events_after[1]["content"]["body"], "with two wrong labels", events_after[1]
+ )
+
+ def test_context_filter_labels_not_labels(self):
+ """Test that we can filter by both a label and the absence of another label."""
+ context_filter = json.dumps(
+ {
+ "types": [EventTypes.Message],
+ "org.matrix.labels": ["#work"],
+ "org.matrix.not_labels": ["#notfun"],
+ }
+ )
+
+ res = self._test_context_filter_labels(context_filter)
+
+ events_before = res["events_before"]
+
+ self.assertEqual(
+ len(events_before), 0, [event["content"] for event in events_before]
+ )
+
+ events_after = res["events_after"]
+
+ self.assertEqual(
+ len(events_after), 1, [event["content"] for event in events_after]
+ )
+ self.assertEqual(
+ events_after[0]["content"]["body"], "with wrong label", events_after[0]
+ )
+
+ def _test_context_filter_labels(self, context_filter):
+ user_id = self.register_user("kermit", "test")
+ tok = self.login("kermit", "test")
+
+ room_id = self.helper.create_room_as(user_id, tok=tok)
+
+ self.helper.send_event(
+ room_id=room_id,
+ type=EventTypes.Message,
+ content={
+ "msgtype": "m.text",
+ "body": "with right label",
+ EventContentFields.LABELS: ["#fun"],
+ },
+ tok=tok,
+ )
+
+ self.helper.send_event(
+ room_id=room_id,
+ type=EventTypes.Message,
+ content={"msgtype": "m.text", "body": "without label"},
+ tok=tok,
+ )
+
+ # The event we'll look up the context for.
+ res = self.helper.send_event(
+ room_id=room_id,
+ type=EventTypes.Message,
+ content={
+ "msgtype": "m.text",
+ "body": "with right label",
+ EventContentFields.LABELS: ["#fun"],
+ },
+ tok=tok,
+ )
+ event_id = res["event_id"]
+
+ self.helper.send_event(
+ room_id=room_id,
+ type=EventTypes.Message,
+ content={
+ "msgtype": "m.text",
+ "body": "with wrong label",
+ EventContentFields.LABELS: ["#work"],
+ },
+ tok=tok,
+ )
+
+ self.helper.send_event(
+ room_id=room_id,
+ type=EventTypes.Message,
+ content={
+ "msgtype": "m.text",
+ "body": "with two wrong labels",
+ EventContentFields.LABELS: ["#work", "#notfun"],
+ },
+ tok=tok,
+ )
+
+ self.helper.send_event(
+ room_id=room_id,
+ type=EventTypes.Message,
+ content={
+ "msgtype": "m.text",
+ "body": "with right label",
+ EventContentFields.LABELS: ["#fun"],
+ },
+ tok=tok,
+ )
+
+ request, channel = self.make_request(
+ "GET",
+ "/rooms/%s/context/%s?filter=%s" % (room_id, event_id, context_filter),
+ access_token=tok,
+ )
+ self.render(request)
+ self.assertEqual(channel.code, 200, channel.result)
+
+ return channel.json_body
+
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