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diff --git a/tests/logging/test_structured.py b/tests/logging/test_structured.py
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+# -*- coding: utf-8 -*-
+# Copyright 2019 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.
+
+import os
+import os.path
+import shutil
+import sys
+import textwrap
+
+from twisted.logger import Logger, eventAsText, eventsFromJSONLogFile
+
+from synapse.config.logger import setup_logging
+from synapse.logging._structured import setup_structured_logging
+from synapse.logging.context import LoggingContext
+
+from tests.unittest import DEBUG, HomeserverTestCase
+
+
+class FakeBeginner(object):
+    def beginLoggingTo(self, observers, **kwargs):
+        self.observers = observers
+
+
+class StructuredLoggingTestCase(HomeserverTestCase):
+    """
+    Tests for Synapse's structured logging support.
+    """
+
+    def test_output_to_json_round_trip(self):
+        """
+        Synapse logs can be outputted to JSON and then read back again.
+        """
+        temp_dir = self.mktemp()
+        os.mkdir(temp_dir)
+        self.addCleanup(shutil.rmtree, temp_dir)
+
+        json_log_file = os.path.abspath(os.path.join(temp_dir, "out.json"))
+
+        log_config = {
+            "drains": {"jsonfile": {"type": "file_json", "location": json_log_file}}
+        }
+
+        # Begin the logger with our config
+        beginner = FakeBeginner()
+        setup_structured_logging(
+            self.hs, self.hs.config, log_config, logBeginner=beginner
+        )
+
+        # Make a logger and send an event
+        logger = Logger(
+            namespace="tests.logging.test_structured", observer=beginner.observers[0]
+        )
+        logger.info("Hello there, {name}!", name="wally")
+
+        # Read the log file and check it has the event we sent
+        with open(json_log_file, "r") as f:
+            logged_events = list(eventsFromJSONLogFile(f))
+        self.assertEqual(len(logged_events), 1)
+
+        # The event pulled from the file should render fine
+        self.assertEqual(
+            eventAsText(logged_events[0], includeTimestamp=False),
+            "[tests.logging.test_structured#info] Hello there, wally!",
+        )
+
+    def test_output_to_text(self):
+        """
+        Synapse logs can be outputted to text.
+        """
+        temp_dir = self.mktemp()
+        os.mkdir(temp_dir)
+        self.addCleanup(shutil.rmtree, temp_dir)
+
+        log_file = os.path.abspath(os.path.join(temp_dir, "out.log"))
+
+        log_config = {"drains": {"file": {"type": "file", "location": log_file}}}
+
+        # Begin the logger with our config
+        beginner = FakeBeginner()
+        setup_structured_logging(
+            self.hs, self.hs.config, log_config, logBeginner=beginner
+        )
+
+        # Make a logger and send an event
+        logger = Logger(
+            namespace="tests.logging.test_structured", observer=beginner.observers[0]
+        )
+        logger.info("Hello there, {name}!", name="wally")
+
+        # Read the log file and check it has the event we sent
+        with open(log_file, "r") as f:
+            logged_events = f.read().strip().split("\n")
+        self.assertEqual(len(logged_events), 1)
+
+        # The event pulled from the file should render fine
+        self.assertTrue(
+            logged_events[0].endswith(
+                " - tests.logging.test_structured - INFO - None - Hello there, wally!"
+            )
+        )
+
+    def test_collects_logcontext(self):
+        """
+        Test that log outputs have the attached logging context.
+        """
+        log_config = {"drains": {}}
+
+        # Begin the logger with our config
+        beginner = FakeBeginner()
+        publisher = setup_structured_logging(
+            self.hs, self.hs.config, log_config, logBeginner=beginner
+        )
+
+        logs = []
+
+        publisher.addObserver(logs.append)
+
+        # Make a logger and send an event
+        logger = Logger(
+            namespace="tests.logging.test_structured", observer=beginner.observers[0]
+        )
+
+        with LoggingContext("testcontext", request="somereq"):
+            logger.info("Hello there, {name}!", name="steve")
+
+        self.assertEqual(len(logs), 1)
+        self.assertEqual(logs[0]["request"], "somereq")
+
+
+class StructuredLoggingConfigurationFileTestCase(HomeserverTestCase):
+    def make_homeserver(self, reactor, clock):
+
+        tempdir = self.mktemp()
+        os.mkdir(tempdir)
+        log_config_file = os.path.abspath(os.path.join(tempdir, "log.config.yaml"))
+        self.homeserver_log = os.path.abspath(os.path.join(tempdir, "homeserver.log"))
+
+        config = self.default_config()
+        config["log_config"] = log_config_file
+
+        with open(log_config_file, "w") as f:
+            f.write(
+                textwrap.dedent(
+                    """\
+                    structured: true
+
+                    drains:
+                        file:
+                            type: file_json
+                            location: %s
+                    """
+                    % (self.homeserver_log,)
+                )
+            )
+
+        self.addCleanup(self._sys_cleanup)
+
+        return self.setup_test_homeserver(config=config)
+
+    def _sys_cleanup(self):
+        sys.stdout = sys.__stdout__
+        sys.stderr = sys.__stderr__
+
+    # Do not remove! We need the logging system to be set other than WARNING.
+    @DEBUG
+    def test_log_output(self):
+        """
+        When a structured logging config is given, Synapse will use it.
+        """
+        setup_logging(self.hs, self.hs.config)
+
+        # Make a logger and send an event
+        logger = Logger(namespace="tests.logging.test_structured")
+
+        with LoggingContext("testcontext", request="somereq"):
+            logger.info("Hello there, {name}!", name="steve")
+
+        with open(self.homeserver_log, "r") as f:
+            logged_events = [
+                eventAsText(x, includeTimestamp=False) for x in eventsFromJSONLogFile(f)
+            ]
+
+        logs = "\n".join(logged_events)
+        self.assertTrue("***** STARTING SERVER *****" in logs)
+        self.assertTrue("Hello there, steve!" in logs)