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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 synapse.rest import admin
+from synapse.rest.client import login, sendtodevice, sync
+
+from tests.unittest import HomeserverTestCase, override_config
+
+
+class SendToDeviceTestCase(HomeserverTestCase):
+    servlets = [
+        admin.register_servlets,
+        login.register_servlets,
+        sendtodevice.register_servlets,
+        sync.register_servlets,
+    ]
+
+    def test_user_to_user(self):
+        """A to-device message from one user to another should get delivered"""
+
+        user1 = self.register_user("u1", "pass")
+        user1_tok = self.login("u1", "pass", "d1")
+
+        user2 = self.register_user("u2", "pass")
+        user2_tok = self.login("u2", "pass", "d2")
+
+        # send the message
+        test_msg = {"foo": "bar"}
+        chan = self.make_request(
+            "PUT",
+            "/_matrix/client/r0/sendToDevice/m.test/1234",
+            content={"messages": {user2: {"d2": test_msg}}},
+            access_token=user1_tok,
+        )
+        self.assertEqual(chan.code, 200, chan.result)
+
+        # check it appears
+        channel = self.make_request("GET", "/sync", access_token=user2_tok)
+        self.assertEqual(channel.code, 200, channel.result)
+        expected_result = {
+            "events": [
+                {
+                    "sender": user1,
+                    "type": "m.test",
+                    "content": test_msg,
+                }
+            ]
+        }
+        self.assertEqual(channel.json_body["to_device"], expected_result)
+
+        # it should re-appear if we do another sync
+        channel = self.make_request("GET", "/sync", access_token=user2_tok)
+        self.assertEqual(channel.code, 200, channel.result)
+        self.assertEqual(channel.json_body["to_device"], expected_result)
+
+        # it should *not* appear if we do an incremental sync
+        sync_token = channel.json_body["next_batch"]
+        channel = self.make_request(
+            "GET", f"/sync?since={sync_token}", access_token=user2_tok
+        )
+        self.assertEqual(channel.code, 200, channel.result)
+        self.assertEqual(channel.json_body.get("to_device", {}).get("events", []), [])
+
+    @override_config({"rc_key_requests": {"per_second": 10, "burst_count": 2}})
+    def test_local_room_key_request(self):
+        """m.room_key_request has special-casing; test from local user"""
+        user1 = self.register_user("u1", "pass")
+        user1_tok = self.login("u1", "pass", "d1")
+
+        user2 = self.register_user("u2", "pass")
+        user2_tok = self.login("u2", "pass", "d2")
+
+        # send three messages
+        for i in range(3):
+            chan = self.make_request(
+                "PUT",
+                f"/_matrix/client/r0/sendToDevice/m.room_key_request/{i}",
+                content={"messages": {user2: {"d2": {"idx": i}}}},
+                access_token=user1_tok,
+            )
+            self.assertEqual(chan.code, 200, chan.result)
+
+        # now sync: we should get two of the three
+        channel = self.make_request("GET", "/sync", access_token=user2_tok)
+        self.assertEqual(channel.code, 200, channel.result)
+        msgs = channel.json_body["to_device"]["events"]
+        self.assertEqual(len(msgs), 2)
+        for i in range(2):
+            self.assertEqual(
+                msgs[i],
+                {"sender": user1, "type": "m.room_key_request", "content": {"idx": i}},
+            )
+        sync_token = channel.json_body["next_batch"]
+
+        # ... time passes
+        self.reactor.advance(1)
+
+        # and we can send more messages
+        chan = self.make_request(
+            "PUT",
+            "/_matrix/client/r0/sendToDevice/m.room_key_request/3",
+            content={"messages": {user2: {"d2": {"idx": 3}}}},
+            access_token=user1_tok,
+        )
+        self.assertEqual(chan.code, 200, chan.result)
+
+        # ... which should arrive
+        channel = self.make_request(
+            "GET", f"/sync?since={sync_token}", access_token=user2_tok
+        )
+        self.assertEqual(channel.code, 200, channel.result)
+        msgs = channel.json_body["to_device"]["events"]
+        self.assertEqual(len(msgs), 1)
+        self.assertEqual(
+            msgs[0],
+            {"sender": user1, "type": "m.room_key_request", "content": {"idx": 3}},
+        )
+
+    @override_config({"rc_key_requests": {"per_second": 10, "burst_count": 2}})
+    def test_remote_room_key_request(self):
+        """m.room_key_request has special-casing; test from remote user"""
+        user2 = self.register_user("u2", "pass")
+        user2_tok = self.login("u2", "pass", "d2")
+
+        federation_registry = self.hs.get_federation_registry()
+
+        # send three messages
+        for i in range(3):
+            self.get_success(
+                federation_registry.on_edu(
+                    "m.direct_to_device",
+                    "remote_server",
+                    {
+                        "sender": "@user:remote_server",
+                        "type": "m.room_key_request",
+                        "messages": {user2: {"d2": {"idx": i}}},
+                        "message_id": f"{i}",
+                    },
+                )
+            )
+
+        # now sync: we should get two of the three
+        channel = self.make_request("GET", "/sync", access_token=user2_tok)
+        self.assertEqual(channel.code, 200, channel.result)
+        msgs = channel.json_body["to_device"]["events"]
+        self.assertEqual(len(msgs), 2)
+        for i in range(2):
+            self.assertEqual(
+                msgs[i],
+                {
+                    "sender": "@user:remote_server",
+                    "type": "m.room_key_request",
+                    "content": {"idx": i},
+                },
+            )
+        sync_token = channel.json_body["next_batch"]
+
+        # ... time passes
+        self.reactor.advance(1)
+
+        # and we can send more messages
+        self.get_success(
+            federation_registry.on_edu(
+                "m.direct_to_device",
+                "remote_server",
+                {
+                    "sender": "@user:remote_server",
+                    "type": "m.room_key_request",
+                    "messages": {user2: {"d2": {"idx": 3}}},
+                    "message_id": "3",
+                },
+            )
+        )
+
+        # ... which should arrive
+        channel = self.make_request(
+            "GET", f"/sync?since={sync_token}", access_token=user2_tok
+        )
+        self.assertEqual(channel.code, 200, channel.result)
+        msgs = channel.json_body["to_device"]["events"]
+        self.assertEqual(len(msgs), 1)
+        self.assertEqual(
+            msgs[0],
+            {
+                "sender": "@user:remote_server",
+                "type": "m.room_key_request",
+                "content": {"idx": 3},
+            },
+        )