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diff --git a/tests/rest/media/test_domain_blocking.py b/tests/rest/media/test_domain_blocking.py
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+# Copyright 2023 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 Dict
+
+from twisted.test.proto_helpers import MemoryReactor
+from twisted.web.resource import Resource
+
+from synapse.media._base import FileInfo
+from synapse.server import HomeServer
+from synapse.util import Clock
+
+from tests import unittest
+from tests.test_utils import SMALL_PNG
+from tests.unittest import override_config
+
+
+class MediaDomainBlockingTests(unittest.HomeserverTestCase):
+    remote_media_id = "doesnotmatter"
+    remote_server_name = "evil.com"
+
+    def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
+        self.store = hs.get_datastores().main
+
+        # Inject a piece of media. We'll use this to ensure we're returning a sane
+        # response when we're not supposed to block it, distinguishing a media block
+        # from a regular 404.
+        file_id = "abcdefg12345"
+        file_info = FileInfo(server_name=self.remote_server_name, file_id=file_id)
+        with hs.get_media_repository().media_storage.store_into_file(file_info) as (
+            f,
+            fname,
+            finish,
+        ):
+            f.write(SMALL_PNG)
+            self.get_success(finish())
+
+        self.get_success(
+            self.store.store_cached_remote_media(
+                origin=self.remote_server_name,
+                media_id=self.remote_media_id,
+                media_type="image/png",
+                media_length=1,
+                time_now_ms=clock.time_msec(),
+                upload_name="test.png",
+                filesystem_id=file_id,
+            )
+        )
+
+    def create_resource_dict(self) -> Dict[str, Resource]:
+        # We need to manually set the resource tree to include media, the
+        # default only does `/_matrix/client` APIs.
+        return {"/_matrix/media": self.hs.get_media_repository_resource()}
+
+    @override_config(
+        {
+            # Disable downloads from the domain we'll be trying to download from.
+            # Should result in a 404.
+            "prevent_media_downloads_from": ["evil.com"]
+        }
+    )
+    def test_cannot_download_blocked_media(self) -> None:
+        """
+        Tests to ensure that remote media which is blocked cannot be downloaded.
+        """
+        response = self.make_request(
+            "GET",
+            f"/_matrix/media/v3/download/evil.com/{self.remote_media_id}",
+            shorthand=False,
+        )
+        self.assertEqual(response.code, 404)
+
+    @override_config(
+        {
+            # Disable downloads from a domain we won't be requesting downloads from.
+            # This proves we haven't broken anything.
+            "prevent_media_downloads_from": ["not-listed.com"]
+        }
+    )
+    def test_remote_media_normally_unblocked(self) -> None:
+        """
+        Tests to ensure that remote media is normally able to be downloaded
+        when no domain block is in place.
+        """
+        response = self.make_request(
+            "GET",
+            f"/_matrix/media/v3/download/evil.com/{self.remote_media_id}",
+            shorthand=False,
+        )
+        self.assertEqual(response.code, 200)
+
+    @override_config(
+        {
+            # Disable downloads from the domain we'll be trying to download from.
+            # Should result in a 404.
+            "prevent_media_downloads_from": ["evil.com"],
+            "dynamic_thumbnails": True,
+        }
+    )
+    def test_cannot_download_blocked_media_thumbnail(self) -> None:
+        """
+        Same test as test_cannot_download_blocked_media but for thumbnails.
+        """
+        response = self.make_request(
+            "GET",
+            f"/_matrix/media/v3/thumbnail/evil.com/{self.remote_media_id}?width=100&height=100",
+            shorthand=False,
+            content={"width": 100, "height": 100},
+        )
+        self.assertEqual(response.code, 404)
+
+    @override_config(
+        {
+            # Disable downloads from a domain we won't be requesting downloads from.
+            # This proves we haven't broken anything.
+            "prevent_media_downloads_from": ["not-listed.com"],
+            "dynamic_thumbnails": True,
+        }
+    )
+    def test_remote_media_thumbnail_normally_unblocked(self) -> None:
+        """
+        Same test as test_remote_media_normally_unblocked but for thumbnails.
+        """
+        response = self.make_request(
+            "GET",
+            f"/_matrix/media/v3/thumbnail/evil.com/{self.remote_media_id}?width=100&height=100",
+            shorthand=False,
+        )
+        self.assertEqual(response.code, 200)