diff --git a/changelog.d/3462.feature b/changelog.d/3462.feature
new file mode 100644
index 000000000..305dbbedd
--- /dev/null
+++ b/changelog.d/3462.feature
@@ -0,0 +1 @@
+Synapse now uses the best performing JSON encoder/decoder according to your runtime (simplejson on CPython, stdlib json on PyPy).
\ No newline at end of file
diff --git a/synapse/api/errors.py b/synapse/api/errors.py
index e6ad3768f..227a0713b 100644
--- a/synapse/api/errors.py
+++ b/synapse/api/errors.py
@@ -17,7 +17,8 @@
 
 import logging
 
-import simplejson as json
+from canonicaljson import json
+
 from six import iteritems
 from six.moves import http_client
 
diff --git a/synapse/api/filtering.py b/synapse/api/filtering.py
index dbc0e7e44..aae25e7a4 100644
--- a/synapse/api/filtering.py
+++ b/synapse/api/filtering.py
@@ -17,7 +17,8 @@ from synapse.storage.presence import UserPresenceState
 from synapse.types import UserID, RoomID
 from twisted.internet import defer
 
-import simplejson as json
+from canonicaljson import json
+
 import jsonschema
 from jsonschema import FormatChecker
 
diff --git a/synapse/crypto/keyclient.py b/synapse/crypto/keyclient.py
index f1fd488b9..2a0eddbea 100644
--- a/synapse/crypto/keyclient.py
+++ b/synapse/crypto/keyclient.py
@@ -18,7 +18,7 @@ from twisted.web.http import HTTPClient
 from twisted.internet.protocol import Factory
 from twisted.internet import defer, reactor
 from synapse.http.endpoint import matrix_federation_endpoint
-import simplejson as json
+from canonicaljson import json
 import logging
 
 
diff --git a/synapse/federation/federation_server.py b/synapse/federation/federation_server.py
index d4dd967c6..a00420a24 100644
--- a/synapse/federation/federation_server.py
+++ b/synapse/federation/federation_server.py
@@ -15,7 +15,7 @@
 # limitations under the License.
 import logging
 
-import simplejson as json
+from canonicaljson import json
 from twisted.internet import defer
 
 from synapse.api.errors import AuthError, FederationError, SynapseError, NotFoundError
diff --git a/synapse/handlers/auth.py b/synapse/handlers/auth.py
index a131b7f73..cbef1f277 100644
--- a/synapse/handlers/auth.py
+++ b/synapse/handlers/auth.py
@@ -16,6 +16,8 @@
 
 from twisted.internet import defer, threads
 
+from canonicaljson import json
+
 from ._base import BaseHandler
 from synapse.api.constants import LoginType
 from synapse.api.errors import (
@@ -32,7 +34,6 @@ from twisted.web.client import PartialDownloadError
 import logging
 import bcrypt
 import pymacaroons
-import simplejson
 import attr
 
 import synapse.util.stringutils as stringutils
@@ -403,7 +404,7 @@ class AuthHandler(BaseHandler):
         except PartialDownloadError as pde:
             # Twisted is silly
             data = pde.response
-            resp_body = simplejson.loads(data)
+            resp_body = json.loads(data)
 
         if 'success' in resp_body:
             # Note that we do NOT check the hostname here: we explicitly
diff --git a/synapse/handlers/e2e_keys.py b/synapse/handlers/e2e_keys.py
index 4d7bf5def..62b4892a4 100644
--- a/synapse/handlers/e2e_keys.py
+++ b/synapse/handlers/e2e_keys.py
@@ -14,10 +14,9 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-import simplejson as json
 import logging
 
-from canonicaljson import encode_canonical_json
+from canonicaljson import encode_canonical_json, json
 from twisted.internet import defer
 from six import iteritems
 
@@ -357,7 +356,7 @@ def _exception_to_failure(e):
     # include ConnectionRefused and other errors
     #
     # Note that some Exceptions (notably twisted's ResponseFailed etc) don't
-    # give a string for e.message, which simplejson then fails to serialize.
+    # give a string for e.message, which json then fails to serialize.
     return {
         "status": 503, "message": str(e.message),
     }
diff --git a/synapse/handlers/identity.py b/synapse/handlers/identity.py
index f00dfe1d3..277c2b776 100644
--- a/synapse/handlers/identity.py
+++ b/synapse/handlers/identity.py
@@ -19,7 +19,7 @@
 
 import logging
 
-import simplejson as json
+from canonicaljson import json
 
 from twisted.internet import defer
 
diff --git a/synapse/handlers/message.py b/synapse/handlers/message.py
index 846728475..cbadf3c88 100644
--- a/synapse/handlers/message.py
+++ b/synapse/handlers/message.py
@@ -14,10 +14,9 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import logging
-import simplejson
 import sys
 
-from canonicaljson import encode_canonical_json
+from canonicaljson import encode_canonical_json, json
 import six
 from six import string_types, itervalues, iteritems
 from twisted.internet import defer
@@ -797,7 +796,7 @@ class EventCreationHandler(object):
         # Ensure that we can round trip before trying to persist in db
         try:
             dump = frozendict_json_encoder.encode(event.content)
-            simplejson.loads(dump)
+            json.loads(dump)
         except Exception:
             logger.exception("Failed to encode content: %r", event.content)
             raise
diff --git a/synapse/http/client.py b/synapse/http/client.py
index 46ffb41de..5bdc484c1 100644
--- a/synapse/http/client.py
+++ b/synapse/http/client.py
@@ -42,7 +42,7 @@ from twisted.web._newclient import ResponseDone
 from six import StringIO
 
 from prometheus_client import Counter
-import simplejson as json
+from canonicaljson import json
 import logging
 import urllib
 
diff --git a/synapse/http/matrixfederationclient.py b/synapse/http/matrixfederationclient.py
index 4e0399e76..2cb9e3e23 100644
--- a/synapse/http/matrixfederationclient.py
+++ b/synapse/http/matrixfederationclient.py
@@ -27,7 +27,7 @@ from synapse.util import logcontext
 from synapse.util.logcontext import make_deferred_yieldable
 import synapse.util.retryutils
 
-from canonicaljson import encode_canonical_json
+from canonicaljson import encode_canonical_json, json
 
 from synapse.api.errors import (
     SynapseError, Codes, HttpResponseException, FederationDeniedError,
@@ -36,7 +36,6 @@ from synapse.api.errors import (
 from signedjson.sign import sign_json
 
 import cgi
-import simplejson as json
 import logging
 import random
 import sys
diff --git a/synapse/http/server.py b/synapse/http/server.py
index bc09b8b2b..517aaf7b5 100644
--- a/synapse/http/server.py
+++ b/synapse/http/server.py
@@ -29,7 +29,7 @@ import synapse.metrics
 import synapse.events
 
 from canonicaljson import (
-    encode_canonical_json, encode_pretty_printed_json
+    encode_canonical_json, encode_pretty_printed_json, json
 )
 
 from twisted.internet import defer
@@ -41,7 +41,6 @@ from twisted.web.util import redirectTo
 import collections
 import logging
 import urllib
-import simplejson
 
 logger = logging.getLogger(__name__)
 
@@ -410,7 +409,7 @@ def respond_with_json(request, code, json_object, send_cors=False,
         if canonical_json or synapse.events.USE_FROZEN_DICTS:
             json_bytes = encode_canonical_json(json_object)
         else:
-            json_bytes = simplejson.dumps(json_object)
+            json_bytes = json.dumps(json_object)
 
     return respond_with_json_bytes(
         request, code, json_bytes,
diff --git a/synapse/http/servlet.py b/synapse/http/servlet.py
index ef8e62901..ef3a01ddc 100644
--- a/synapse/http/servlet.py
+++ b/synapse/http/servlet.py
@@ -18,7 +18,9 @@
 from synapse.api.errors import SynapseError, Codes
 
 import logging
-import simplejson
+
+from canonicaljson import json
+
 
 logger = logging.getLogger(__name__)
 
@@ -171,7 +173,7 @@ def parse_json_value_from_request(request, allow_empty_body=False):
         return None
 
     try:
-        content = simplejson.loads(content_bytes)
+        content = json.loads(content_bytes)
     except Exception as e:
         logger.warn("Unable to parse JSON: %s", e)
         raise SynapseError(400, "Content not JSON.", errcode=Codes.NOT_JSON)
diff --git a/synapse/metrics/__init__.py b/synapse/metrics/__init__.py
index 7d6e0232e..2d2397caa 100644
--- a/synapse/metrics/__init__.py
+++ b/synapse/metrics/__init__.py
@@ -147,7 +147,8 @@ class GCCounts(object):
         yield cm
 
 
-REGISTRY.register(GCCounts())
+if not running_on_pypy:
+    REGISTRY.register(GCCounts())
 
 #
 # Twisted reactor metrics
diff --git a/synapse/replication/tcp/commands.py b/synapse/replication/tcp/commands.py
index 12aac3cc6..f3908df64 100644
--- a/synapse/replication/tcp/commands.py
+++ b/synapse/replication/tcp/commands.py
@@ -19,13 +19,17 @@ allowed to be sent by which side.
 """
 
 import logging
-import simplejson
+import platform
 
+if platform.python_implementation() == "PyPy":
+    import json
+    _json_encoder = json.JSONEncoder()
+else:
+    import simplejson as json
+    _json_encoder = json.JSONEncoder(namedtuple_as_object=False)
 
 logger = logging.getLogger(__name__)
 
-_json_encoder = simplejson.JSONEncoder(namedtuple_as_object=False)
-
 
 class Command(object):
     """The base command class.
@@ -102,7 +106,7 @@ class RdataCommand(Command):
         return cls(
             stream_name,
             None if token == "batch" else int(token),
-            simplejson.loads(row_json)
+            json.loads(row_json)
         )
 
     def to_line(self):
@@ -300,7 +304,7 @@ class InvalidateCacheCommand(Command):
     def from_line(cls, line):
         cache_func, keys_json = line.split(" ", 1)
 
-        return cls(cache_func, simplejson.loads(keys_json))
+        return cls(cache_func, json.loads(keys_json))
 
     def to_line(self):
         return " ".join((
@@ -329,7 +333,7 @@ class UserIpCommand(Command):
     def from_line(cls, line):
         user_id, jsn = line.split(" ", 1)
 
-        access_token, ip, user_agent, device_id, last_seen = simplejson.loads(jsn)
+        access_token, ip, user_agent, device_id, last_seen = json.loads(jsn)
 
         return cls(
             user_id, access_token, ip, user_agent, device_id, last_seen
diff --git a/synapse/rest/client/v1/login.py b/synapse/rest/client/v1/login.py
index 34df5be4e..88ca5184c 100644
--- a/synapse/rest/client/v1/login.py
+++ b/synapse/rest/client/v1/login.py
@@ -23,7 +23,8 @@ from synapse.util.msisdn import phone_number_to_msisdn
 
 from .base import ClientV1RestServlet, client_path_patterns
 
-import simplejson as json
+from canonicaljson import json
+
 import urllib
 from six.moves.urllib import parse as urlparse
 
diff --git a/synapse/rest/client/v1/room.py b/synapse/rest/client/v1/room.py
index 0b984987e..e6ae5db79 100644
--- a/synapse/rest/client/v1/room.py
+++ b/synapse/rest/client/v1/room.py
@@ -31,7 +31,7 @@ from synapse.http.servlet import (
 from six.moves.urllib import parse as urlparse
 
 import logging
-import simplejson as json
+from canonicaljson import json
 
 logger = logging.getLogger(__name__)
 
diff --git a/synapse/rest/client/v2_alpha/sync.py b/synapse/rest/client/v2_alpha/sync.py
index a291cffbf..d2aa47b32 100644
--- a/synapse/rest/client/v2_alpha/sync.py
+++ b/synapse/rest/client/v2_alpha/sync.py
@@ -33,7 +33,7 @@ from ._base import set_timeline_upper_limit
 import itertools
 import logging
 
-import simplejson as json
+from canonicaljson import json
 
 logger = logging.getLogger(__name__)
 
diff --git a/synapse/rest/media/v0/content_repository.py b/synapse/rest/media/v0/content_repository.py
index 956bd5da7..e44d4276d 100644
--- a/synapse/rest/media/v0/content_repository.py
+++ b/synapse/rest/media/v0/content_repository.py
@@ -22,8 +22,9 @@ from synapse.api.errors import (
 from twisted.protocols.basic import FileSender
 from twisted.web import server, resource
 
+from canonicaljson import json
+
 import base64
-import simplejson as json
 import logging
 import os
 import re
diff --git a/synapse/rest/media/v1/preview_url_resource.py b/synapse/rest/media/v1/preview_url_resource.py
index 565cef2b8..adca49064 100644
--- a/synapse/rest/media/v1/preview_url_resource.py
+++ b/synapse/rest/media/v1/preview_url_resource.py
@@ -23,7 +23,8 @@ import re
 import shutil
 import sys
 import traceback
-import simplejson as json
+
+from canonicaljson import json
 
 from six.moves import urllib_parse as urlparse
 from six import string_types
diff --git a/synapse/storage/account_data.py b/synapse/storage/account_data.py
index 284ec3c97..7034a6139 100644
--- a/synapse/storage/account_data.py
+++ b/synapse/storage/account_data.py
@@ -22,8 +22,9 @@ from synapse.storage.util.id_generators import StreamIdGenerator
 from synapse.util.caches.stream_change_cache import StreamChangeCache
 from synapse.util.caches.descriptors import cached, cachedInlineCallbacks
 
+from canonicaljson import json
+
 import abc
-import simplejson as json
 import logging
 
 logger = logging.getLogger(__name__)
diff --git a/synapse/storage/appservice.py b/synapse/storage/appservice.py
index 12ea8a158..4d32d0bdf 100644
--- a/synapse/storage/appservice.py
+++ b/synapse/storage/appservice.py
@@ -15,8 +15,8 @@
 # limitations under the License.
 import logging
 import re
-import simplejson as json
 from twisted.internet import defer
+from canonicaljson import json
 
 from synapse.appservice import AppServiceTransaction
 from synapse.config.appservice import load_appservices
diff --git a/synapse/storage/background_updates.py b/synapse/storage/background_updates.py
index b7e9c716c..af1896451 100644
--- a/synapse/storage/background_updates.py
+++ b/synapse/storage/background_updates.py
@@ -18,7 +18,8 @@ from . import engines
 
 from twisted.internet import defer
 
-import simplejson as json
+from canonicaljson import json
+
 import logging
 
 logger = logging.getLogger(__name__)
diff --git a/synapse/storage/deviceinbox.py b/synapse/storage/deviceinbox.py
index a879e5bfc..38addbf9c 100644
--- a/synapse/storage/deviceinbox.py
+++ b/synapse/storage/deviceinbox.py
@@ -14,7 +14,8 @@
 # limitations under the License.
 
 import logging
-import simplejson
+
+from canonicaljson import json
 
 from twisted.internet import defer
 
@@ -85,7 +86,7 @@ class DeviceInboxStore(BackgroundUpdateStore):
             )
             rows = []
             for destination, edu in remote_messages_by_destination.items():
-                edu_json = simplejson.dumps(edu)
+                edu_json = json.dumps(edu)
                 rows.append((destination, stream_id, now_ms, edu_json))
             txn.executemany(sql, rows)
 
@@ -177,7 +178,7 @@ class DeviceInboxStore(BackgroundUpdateStore):
                     " WHERE user_id = ?"
                 )
                 txn.execute(sql, (user_id,))
-                message_json = simplejson.dumps(messages_by_device["*"])
+                message_json = json.dumps(messages_by_device["*"])
                 for row in txn:
                     # Add the message for all devices for this user on this
                     # server.
@@ -199,7 +200,7 @@ class DeviceInboxStore(BackgroundUpdateStore):
                     # Only insert into the local inbox if the device exists on
                     # this server
                     device = row[0]
-                    message_json = simplejson.dumps(messages_by_device[device])
+                    message_json = json.dumps(messages_by_device[device])
                     messages_json_for_user[device] = message_json
 
             if messages_json_for_user:
@@ -253,7 +254,7 @@ class DeviceInboxStore(BackgroundUpdateStore):
             messages = []
             for row in txn:
                 stream_pos = row[0]
-                messages.append(simplejson.loads(row[1]))
+                messages.append(json.loads(row[1]))
             if len(messages) < limit:
                 stream_pos = current_stream_id
             return (messages, stream_pos)
@@ -389,7 +390,7 @@ class DeviceInboxStore(BackgroundUpdateStore):
             messages = []
             for row in txn:
                 stream_pos = row[0]
-                messages.append(simplejson.loads(row[1]))
+                messages.append(json.loads(row[1]))
             if len(messages) < limit:
                 stream_pos = current_stream_id
             return (messages, stream_pos)
diff --git a/synapse/storage/devices.py b/synapse/storage/devices.py
index d149d8392..2ed9ada78 100644
--- a/synapse/storage/devices.py
+++ b/synapse/storage/devices.py
@@ -13,7 +13,6 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import logging
-import simplejson as json
 
 from twisted.internet import defer
 
@@ -21,6 +20,8 @@ from synapse.api.errors import StoreError
 from ._base import SQLBaseStore, Cache
 from synapse.util.caches.descriptors import cached, cachedList, cachedInlineCallbacks
 
+from canonicaljson import json
+
 from six import itervalues, iteritems
 
 logger = logging.getLogger(__name__)
diff --git a/synapse/storage/end_to_end_keys.py b/synapse/storage/end_to_end_keys.py
index b14648794..181047c8b 100644
--- a/synapse/storage/end_to_end_keys.py
+++ b/synapse/storage/end_to_end_keys.py
@@ -16,8 +16,7 @@ from twisted.internet import defer
 
 from synapse.util.caches.descriptors import cached
 
-from canonicaljson import encode_canonical_json
-import simplejson as json
+from canonicaljson import encode_canonical_json, json
 
 from ._base import SQLBaseStore
 
diff --git a/synapse/storage/event_push_actions.py b/synapse/storage/event_push_actions.py
index 8cb24b7d5..05cb3f61c 100644
--- a/synapse/storage/event_push_actions.py
+++ b/synapse/storage/event_push_actions.py
@@ -19,7 +19,8 @@ from twisted.internet import defer
 from synapse.util.caches.descriptors import cachedInlineCallbacks
 
 import logging
-import simplejson as json
+
+from canonicaljson import json
 
 from six import iteritems
 
diff --git a/synapse/storage/events.py b/synapse/storage/events.py
index 7d0e59538..d816d4883 100644
--- a/synapse/storage/events.py
+++ b/synapse/storage/events.py
@@ -19,7 +19,8 @@ from functools import wraps
 import itertools
 import logging
 
-import simplejson as json
+from canonicaljson import json
+
 from twisted.internet import defer
 
 from synapse.storage.events_worker import EventsWorkerStore
diff --git a/synapse/storage/events_worker.py b/synapse/storage/events_worker.py
index f6a6e46b4..896225aab 100644
--- a/synapse/storage/events_worker.py
+++ b/synapse/storage/events_worker.py
@@ -29,7 +29,8 @@ from synapse.api.errors import SynapseError
 from collections import namedtuple
 
 import logging
-import simplejson as json
+
+from canonicaljson import json
 
 # these are only included to make the type annotations work
 from synapse.events import EventBase    # noqa: F401
diff --git a/synapse/storage/filtering.py b/synapse/storage/filtering.py
index 2e2763126..eae6027ce 100644
--- a/synapse/storage/filtering.py
+++ b/synapse/storage/filtering.py
@@ -19,8 +19,7 @@ from ._base import SQLBaseStore
 from synapse.api.errors import SynapseError, Codes
 from synapse.util.caches.descriptors import cachedInlineCallbacks
 
-from canonicaljson import encode_canonical_json
-import simplejson as json
+from canonicaljson import encode_canonical_json, json
 
 
 class FilteringStore(SQLBaseStore):
diff --git a/synapse/storage/group_server.py b/synapse/storage/group_server.py
index da05ccb02..b77402d29 100644
--- a/synapse/storage/group_server.py
+++ b/synapse/storage/group_server.py
@@ -20,7 +20,7 @@ from synapse.api.errors import SynapseError
 
 from ._base import SQLBaseStore
 
-import simplejson as json
+from canonicaljson import json
 
 
 # The category ID for the "default" category. We don't store as null in the
diff --git a/synapse/storage/push_rule.py b/synapse/storage/push_rule.py
index 04a0b59a3..9e52e992b 100644
--- a/synapse/storage/push_rule.py
+++ b/synapse/storage/push_rule.py
@@ -25,9 +25,10 @@ from synapse.push.baserules import list_with_base_rules
 from synapse.api.constants import EventTypes
 from twisted.internet import defer
 
+from canonicaljson import json
+
 import abc
 import logging
-import simplejson as json
 
 logger = logging.getLogger(__name__)
 
diff --git a/synapse/storage/pusher.py b/synapse/storage/pusher.py
index 307660b99..c6def861c 100644
--- a/synapse/storage/pusher.py
+++ b/synapse/storage/pusher.py
@@ -17,12 +17,11 @@
 from ._base import SQLBaseStore
 from twisted.internet import defer
 
-from canonicaljson import encode_canonical_json
+from canonicaljson import encode_canonical_json, json
 
 from synapse.util.caches.descriptors import cachedInlineCallbacks, cachedList
 
 import logging
-import simplejson as json
 import types
 
 logger = logging.getLogger(__name__)
diff --git a/synapse/storage/receipts.py b/synapse/storage/receipts.py
index c93c228f6..f230a3bab 100644
--- a/synapse/storage/receipts.py
+++ b/synapse/storage/receipts.py
@@ -21,9 +21,10 @@ from synapse.util.caches.stream_change_cache import StreamChangeCache
 
 from twisted.internet import defer
 
+from canonicaljson import json
+
 import abc
 import logging
-import simplejson as json
 
 
 logger = logging.getLogger(__name__)
diff --git a/synapse/storage/room.py b/synapse/storage/room.py
index ea6a18918..ca0eb187e 100644
--- a/synapse/storage/room.py
+++ b/synapse/storage/room.py
@@ -20,9 +20,10 @@ from synapse.storage._base import SQLBaseStore
 from synapse.storage.search import SearchStore
 from synapse.util.caches.descriptors import cached, cachedInlineCallbacks
 
+from canonicaljson import json
+
 import collections
 import logging
-import simplejson as json
 import re
 
 logger = logging.getLogger(__name__)
diff --git a/synapse/storage/roommember.py b/synapse/storage/roommember.py
index 829cc4a20..8fc9549a7 100644
--- a/synapse/storage/roommember.py
+++ b/synapse/storage/roommember.py
@@ -28,7 +28,7 @@ from synapse.api.constants import Membership, EventTypes
 from synapse.types import get_domain_from_id
 
 import logging
-import simplejson as json
+from canonicaljson import json
 
 from six import itervalues, iteritems
 
diff --git a/synapse/storage/search.py b/synapse/storage/search.py
index f0fa5d763..9b77c4531 100644
--- a/synapse/storage/search.py
+++ b/synapse/storage/search.py
@@ -16,7 +16,7 @@
 from collections import namedtuple
 import logging
 import re
-import simplejson as json
+from canonicaljson import json
 
 from six import string_types
 
diff --git a/synapse/storage/tags.py b/synapse/storage/tags.py
index 6671d3cfc..04d123ed9 100644
--- a/synapse/storage/tags.py
+++ b/synapse/storage/tags.py
@@ -19,7 +19,8 @@ from synapse.storage.account_data import AccountDataWorkerStore
 from synapse.util.caches.descriptors import cached
 from twisted.internet import defer
 
-import simplejson as json
+from canonicaljson import json
+
 import logging
 
 from six.moves import range
diff --git a/synapse/storage/transactions.py b/synapse/storage/transactions.py
index e485d19b8..acbc03446 100644
--- a/synapse/storage/transactions.py
+++ b/synapse/storage/transactions.py
@@ -19,12 +19,11 @@ from synapse.util.caches.descriptors import cached
 from twisted.internet import defer
 import six
 
-from canonicaljson import encode_canonical_json
+from canonicaljson import encode_canonical_json, json
 
 from collections import namedtuple
 
 import logging
-import simplejson as json
 
 # py2 sqlite has buffer hardcoded as only binary type, so we must use it,
 # despite being deprecated and removed in favor of memoryview
diff --git a/synapse/util/frozenutils.py b/synapse/util/frozenutils.py
index 15f0a7ba9..535e7d0e7 100644
--- a/synapse/util/frozenutils.py
+++ b/synapse/util/frozenutils.py
@@ -14,7 +14,7 @@
 # limitations under the License.
 
 from frozendict import frozendict
-import simplejson as json
+from canonicaljson import json
 
 from six import string_types