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-rw-r--r--synapse/api/auth.py4
-rwxr-xr-xsynapse/app/homeserver.py56
-rw-r--r--synapse/config/_base.py4
-rw-r--r--synapse/config/server.py15
-rw-r--r--synapse/config/tls.py115
-rw-r--r--synapse/crypto/context_factory.py15
-rw-r--r--synapse/handlers/acme.py147
-rw-r--r--synapse/handlers/room_list.py14
-rw-r--r--synapse/handlers/user_directory.py6
-rw-r--r--synapse/http/client.py5
-rw-r--r--synapse/http/endpoint.py144
-rw-r--r--synapse/http/federation/matrix_federation_agent.py125
-rw-r--r--synapse/http/federation/srv_resolver.py167
-rw-r--r--synapse/http/matrixfederationclient.py37
-rw-r--r--synapse/python_dependencies.py4
-rw-r--r--synapse/rest/client/v2_alpha/register.py7
-rw-r--r--synapse/server.py5
-rw-r--r--synapse/storage/_base.py171
-rw-r--r--synapse/storage/client_ips.py11
-rw-r--r--synapse/storage/engines/__init__.py2
-rw-r--r--synapse/storage/engines/postgres.py14
-rw-r--r--synapse/storage/engines/sqlite.py (renamed from synapse/storage/engines/sqlite3.py)9
-rw-r--r--synapse/storage/pusher.py9
-rw-r--r--synapse/storage/user_directory.py55
24 files changed, 827 insertions, 314 deletions
diff --git a/synapse/api/auth.py b/synapse/api/auth.py
index ba1019b9b2..e37b807c94 100644
--- a/synapse/api/auth.py
+++ b/synapse/api/auth.py
@@ -819,7 +819,9 @@ class Auth(object):
             elif threepid:
                 # If the user does not exist yet, but is signing up with a
                 # reserved threepid then pass auth check
-                if is_threepid_reserved(self.hs.config, threepid):
+                if is_threepid_reserved(
+                    self.hs.config.mau_limits_reserved_threepids, threepid
+                ):
                     return
             # Else if there is no room in the MAU bucket, bail
             current_mau = yield self.store.get_monthly_active_count()
diff --git a/synapse/app/homeserver.py b/synapse/app/homeserver.py
index f3ac3d19f0..ffc49d77cc 100755
--- a/synapse/app/homeserver.py
+++ b/synapse/app/homeserver.py
@@ -13,10 +13,12 @@
 # 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 gc
 import logging
 import os
 import sys
+import traceback
 
 from six import iteritems
 
@@ -324,17 +326,12 @@ def setup(config_options):
 
     events.USE_FROZEN_DICTS = config.use_frozen_dicts
 
-    tls_server_context_factory = context_factory.ServerContextFactory(config)
-    tls_client_options_factory = context_factory.ClientTLSOptionsFactory(config)
-
     database_engine = create_engine(config.database_config)
     config.database_config["args"]["cp_openfun"] = database_engine.on_new_connection
 
     hs = SynapseHomeServer(
         config.server_name,
         db_config=config.database_config,
-        tls_server_context_factory=tls_server_context_factory,
-        tls_client_options_factory=tls_client_options_factory,
         config=config,
         version_string="Synapse/" + get_version_string(synapse),
         database_engine=database_engine,
@@ -361,12 +358,53 @@ def setup(config_options):
     logger.info("Database prepared in %s.", config.database_config['name'])
 
     hs.setup()
-    hs.start_listening()
 
+    @defer.inlineCallbacks
     def start():
-        hs.get_pusherpool().start()
-        hs.get_datastore().start_profiling()
-        hs.get_datastore().start_doing_background_updates()
+        try:
+            # Check if the certificate is still valid.
+            cert_days_remaining = hs.config.is_disk_cert_valid()
+
+            if hs.config.acme_enabled:
+                # If ACME is enabled, we might need to provision a certificate
+                # before starting.
+                acme = hs.get_acme_handler()
+
+                # Start up the webservices which we will respond to ACME
+                # challenges with.
+                yield acme.start_listening()
+
+                # We want to reprovision if cert_days_remaining is None (meaning no
+                # certificate exists), or the days remaining number it returns
+                # is less than our re-registration threshold.
+                if (cert_days_remaining is None) or (
+                    not cert_days_remaining > hs.config.acme_reprovision_threshold
+                ):
+                    yield acme.provision_certificate()
+
+            # Read the certificate from disk and build the context factories for
+            # TLS.
+            hs.config.read_certificate_from_disk()
+            hs.tls_server_context_factory = context_factory.ServerContextFactory(config)
+            hs.tls_client_options_factory = context_factory.ClientTLSOptionsFactory(
+                config
+            )
+
+            # It is now safe to start your Synapse.
+            hs.start_listening()
+            hs.get_pusherpool().start()
+            hs.get_datastore().start_profiling()
+            hs.get_datastore().start_doing_background_updates()
+        except Exception as e:
+            # If a DeferredList failed (like in listening on the ACME listener),
+            # we need to print the subfailure explicitly.
+            if isinstance(e, defer.FirstError):
+                e.subFailure.printTraceback(sys.stderr)
+                sys.exit(1)
+
+            # Something else went wrong when starting. Print it and bail out.
+            traceback.print_exc(file=sys.stderr)
+            sys.exit(1)
 
     reactor.callWhenRunning(start)
 
diff --git a/synapse/config/_base.py b/synapse/config/_base.py
index fd2d6d52ef..5858fb92b4 100644
--- a/synapse/config/_base.py
+++ b/synapse/config/_base.py
@@ -367,7 +367,7 @@ class Config(object):
         if not keys_directory:
             keys_directory = os.path.dirname(config_files[-1])
 
-        config_dir_path = os.path.abspath(keys_directory)
+        self.config_dir_path = os.path.abspath(keys_directory)
 
         specified_config = {}
         for config_file in config_files:
@@ -379,7 +379,7 @@ class Config(object):
 
         server_name = specified_config["server_name"]
         config_string = self.generate_config(
-            config_dir_path=config_dir_path,
+            config_dir_path=self.config_dir_path,
             data_dir_path=os.getcwd(),
             server_name=server_name,
             generate_secrets=False,
diff --git a/synapse/config/server.py b/synapse/config/server.py
index fb57791098..22dcc87d8a 100644
--- a/synapse/config/server.py
+++ b/synapse/config/server.py
@@ -256,7 +256,11 @@ class ServerConfig(Config):
         #
         # web_client_location: "/path/to/web/root"
 
-        # The public-facing base URL for the client API (not including _matrix/...)
+        # The public-facing base URL that clients use to access this HS
+        # (not including _matrix/...). This is the same URL a user would
+        # enter into the 'custom HS URL' field on their client. If you
+        # use synapse with a reverse proxy, this should be the URL to reach
+        # synapse via the proxy.
         # public_baseurl: https://example.com:8448/
 
         # Set the soft limit on the number of file descriptors synapse can use
@@ -420,19 +424,18 @@ class ServerConfig(Config):
                                   " service on the given port.")
 
 
-def is_threepid_reserved(config, threepid):
+def is_threepid_reserved(reserved_threepids, threepid):
     """Check the threepid against the reserved threepid config
     Args:
-        config(ServerConfig) - to access server config attributes
+        reserved_threepids([dict]) - list of reserved threepids
         threepid(dict) - The threepid to test for
 
     Returns:
         boolean Is the threepid undertest reserved_user
     """
 
-    for tp in config.mau_limits_reserved_threepids:
-        if (threepid['medium'] == tp['medium']
-                and threepid['address'] == tp['address']):
+    for tp in reserved_threepids:
+        if (threepid['medium'] == tp['medium'] and threepid['address'] == tp['address']):
             return True
     return False
 
diff --git a/synapse/config/tls.py b/synapse/config/tls.py
index bb8952c672..a75e233aa0 100644
--- a/synapse/config/tls.py
+++ b/synapse/config/tls.py
@@ -13,60 +13,110 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+import logging
 import os
+from datetime import datetime
 from hashlib import sha256
 
 from unpaddedbase64 import encode_base64
 
 from OpenSSL import crypto
 
-from ._base import Config
+from synapse.config._base import Config
+
+logger = logging.getLogger()
 
 
 class TlsConfig(Config):
     def read_config(self, config):
-        self.tls_certificate = self.read_tls_certificate(
-            config.get("tls_certificate_path")
-        )
-        self.tls_certificate_file = config.get("tls_certificate_path")
 
+        acme_config = config.get("acme", {})
+        self.acme_enabled = acme_config.get("enabled", False)
+        self.acme_url = acme_config.get(
+            "url", "https://acme-v01.api.letsencrypt.org/directory"
+        )
+        self.acme_port = acme_config.get("port", 8449)
+        self.acme_bind_addresses = acme_config.get("bind_addresses", ["127.0.0.1"])
+        self.acme_reprovision_threshold = acme_config.get("reprovision_threshold", 30)
+
+        self.tls_certificate_file = os.path.abspath(config.get("tls_certificate_path"))
+        self.tls_private_key_file = os.path.abspath(config.get("tls_private_key_path"))
+        self._original_tls_fingerprints = config["tls_fingerprints"]
+        self.tls_fingerprints = list(self._original_tls_fingerprints)
         self.no_tls = config.get("no_tls", False)
 
-        if self.no_tls:
-            self.tls_private_key = None
-        else:
-            self.tls_private_key = self.read_tls_private_key(
-                config.get("tls_private_key_path")
-            )
+        # This config option applies to non-federation HTTP clients
+        # (e.g. for talking to recaptcha, identity servers, and such)
+        # It should never be used in production, and is intended for
+        # use only when running tests.
+        self.use_insecure_ssl_client_just_for_testing_do_not_use = config.get(
+            "use_insecure_ssl_client_just_for_testing_do_not_use"
+        )
+
+        self.tls_certificate = None
+        self.tls_private_key = None
+
+    def is_disk_cert_valid(self):
+        """
+        Is the certificate we have on disk valid, and if so, for how long?
+
+        Returns:
+            int: Days remaining of certificate validity.
+            None: No certificate exists.
+        """
+        if not os.path.exists(self.tls_certificate_file):
+            return None
+
+        try:
+            with open(self.tls_certificate_file, 'rb') as f:
+                cert_pem = f.read()
+        except Exception:
+            logger.exception("Failed to read existing certificate off disk!")
+            raise
+
+        try:
+            tls_certificate = crypto.load_certificate(crypto.FILETYPE_PEM, cert_pem)
+        except Exception:
+            logger.exception("Failed to parse existing certificate off disk!")
+            raise
+
+        # YYYYMMDDhhmmssZ -- in UTC
+        expires_on = datetime.strptime(
+            tls_certificate.get_notAfter().decode('ascii'), "%Y%m%d%H%M%SZ"
+        )
+        now = datetime.utcnow()
+        days_remaining = (expires_on - now).days
+        return days_remaining
 
-        self.tls_fingerprints = config["tls_fingerprints"]
+    def read_certificate_from_disk(self):
+        """
+        Read the certificates from disk.
+        """
+        self.tls_certificate = self.read_tls_certificate(self.tls_certificate_file)
+
+        if not self.no_tls:
+            self.tls_private_key = self.read_tls_private_key(self.tls_private_key_file)
+
+        self.tls_fingerprints = list(self._original_tls_fingerprints)
 
         # Check that our own certificate is included in the list of fingerprints
         # and include it if it is not.
         x509_certificate_bytes = crypto.dump_certificate(
-            crypto.FILETYPE_ASN1,
-            self.tls_certificate
+            crypto.FILETYPE_ASN1, self.tls_certificate
         )
         sha256_fingerprint = encode_base64(sha256(x509_certificate_bytes).digest())
         sha256_fingerprints = set(f["sha256"] for f in self.tls_fingerprints)
         if sha256_fingerprint not in sha256_fingerprints:
             self.tls_fingerprints.append({u"sha256": sha256_fingerprint})
 
-        # This config option applies to non-federation HTTP clients
-        # (e.g. for talking to recaptcha, identity servers, and such)
-        # It should never be used in production, and is intended for
-        # use only when running tests.
-        self.use_insecure_ssl_client_just_for_testing_do_not_use = config.get(
-            "use_insecure_ssl_client_just_for_testing_do_not_use"
-        )
-
     def default_config(self, config_dir_path, server_name, **kwargs):
         base_key_name = os.path.join(config_dir_path, server_name)
 
         tls_certificate_path = base_key_name + ".tls.crt"
         tls_private_key_path = base_key_name + ".tls.key"
 
-        return """\
+        return (
+            """\
         # PEM encoded X509 certificate for TLS.
         # You can replace the self-signed certificate that synapse
         # autogenerates on launch with your own SSL certificate + key pair
@@ -107,7 +157,24 @@ class TlsConfig(Config):
         #
         tls_fingerprints: []
         # tls_fingerprints: [{"sha256": "<base64_encoded_sha256_fingerprint>"}]
-        """ % locals()
+
+        ## Support for ACME certificate auto-provisioning.
+        # acme:
+        #    enabled: false
+        ##   ACME path.
+        ##   If you only want to test, use the staging url:
+        ##   https://acme-staging.api.letsencrypt.org/directory
+        #    url: 'https://acme-v01.api.letsencrypt.org/directory'
+        ##   Port number (to listen for the HTTP-01 challenge).
+        ##   Using port 80 requires utilising something like authbind, or proxying to it.
+        #    port: 8449
+        ##   Hosts to bind to.
+        #    bind_addresses: ['127.0.0.1']
+        ##   How many days remaining on a certificate before it is renewed.
+        #    reprovision_threshold: 30
+        """
+            % locals()
+        )
 
     def read_tls_certificate(self, cert_path):
         cert_pem = self.read_file(cert_path, "tls_certificate")
diff --git a/synapse/crypto/context_factory.py b/synapse/crypto/context_factory.py
index 6ba3eca7b2..286ad80100 100644
--- a/synapse/crypto/context_factory.py
+++ b/synapse/crypto/context_factory.py
@@ -17,6 +17,7 @@ from zope.interface import implementer
 
 from OpenSSL import SSL, crypto
 from twisted.internet._sslverify import _defaultCurveName
+from twisted.internet.abstract import isIPAddress, isIPv6Address
 from twisted.internet.interfaces import IOpenSSLClientConnectionCreator
 from twisted.internet.ssl import CertificateOptions, ContextFactory
 from twisted.python.failure import Failure
@@ -98,8 +99,14 @@ class ClientTLSOptions(object):
 
     def __init__(self, hostname, ctx):
         self._ctx = ctx
-        self._hostname = hostname
-        self._hostnameBytes = _idnaBytes(hostname)
+
+        if isIPAddress(hostname) or isIPv6Address(hostname):
+            self._hostnameBytes = hostname.encode('ascii')
+            self._sendSNI = False
+        else:
+            self._hostnameBytes = _idnaBytes(hostname)
+            self._sendSNI = True
+
         ctx.set_info_callback(
             _tolerateErrors(self._identityVerifyingInfoCallback)
         )
@@ -111,7 +118,9 @@ class ClientTLSOptions(object):
         return connection
 
     def _identityVerifyingInfoCallback(self, connection, where, ret):
-        if where & SSL.SSL_CB_HANDSHAKE_START:
+        # Literal IPv4 and IPv6 addresses are not permitted
+        # as host names according to the RFCs
+        if where & SSL.SSL_CB_HANDSHAKE_START and self._sendSNI:
             connection.set_tlsext_host_name(self._hostnameBytes)
 
 
diff --git a/synapse/handlers/acme.py b/synapse/handlers/acme.py
new file mode 100644
index 0000000000..73ea7ed018
--- /dev/null
+++ b/synapse/handlers/acme.py
@@ -0,0 +1,147 @@
+# -*- coding: utf-8 -*-
+# Copyright 2019 New Vector Ltd
+#
+# 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 logging
+
+import attr
+from zope.interface import implementer
+
+from twisted.internet import defer
+from twisted.internet.endpoints import serverFromString
+from twisted.python.filepath import FilePath
+from twisted.python.url import URL
+from twisted.web import server, static
+from twisted.web.resource import Resource
+
+logger = logging.getLogger(__name__)
+
+try:
+    from txacme.interfaces import ICertificateStore
+
+    @attr.s
+    @implementer(ICertificateStore)
+    class ErsatzStore(object):
+        """
+        A store that only stores in memory.
+        """
+
+        certs = attr.ib(default=attr.Factory(dict))
+
+        def store(self, server_name, pem_objects):
+            self.certs[server_name] = [o.as_bytes() for o in pem_objects]
+            return defer.succeed(None)
+
+
+except ImportError:
+    # txacme is missing
+    pass
+
+
+class AcmeHandler(object):
+    def __init__(self, hs):
+        self.hs = hs
+        self.reactor = hs.get_reactor()
+
+    @defer.inlineCallbacks
+    def start_listening(self):
+
+        # Configure logging for txacme, if you need to debug
+        # from eliot import add_destinations
+        # from eliot.twisted import TwistedDestination
+        #
+        # add_destinations(TwistedDestination())
+
+        from txacme.challenges import HTTP01Responder
+        from txacme.service import AcmeIssuingService
+        from txacme.endpoint import load_or_create_client_key
+        from txacme.client import Client
+        from josepy.jwa import RS256
+
+        self._store = ErsatzStore()
+        responder = HTTP01Responder()
+
+        self._issuer = AcmeIssuingService(
+            cert_store=self._store,
+            client_creator=(
+                lambda: Client.from_url(
+                    reactor=self.reactor,
+                    url=URL.from_text(self.hs.config.acme_url),
+                    key=load_or_create_client_key(
+                        FilePath(self.hs.config.config_dir_path)
+                    ),
+                    alg=RS256,
+                )
+            ),
+            clock=self.reactor,
+            responders=[responder],
+        )
+
+        well_known = Resource()
+        well_known.putChild(b'acme-challenge', responder.resource)
+        responder_resource = Resource()
+        responder_resource.putChild(b'.well-known', well_known)
+        responder_resource.putChild(b'check', static.Data(b'OK', b'text/plain'))
+
+        srv = server.Site(responder_resource)
+
+        listeners = []
+
+        for host in self.hs.config.acme_bind_addresses:
+            logger.info(
+                "Listening for ACME requests on %s:%s", host, self.hs.config.acme_port
+            )
+            endpoint = serverFromString(
+                self.reactor, "tcp:%s:interface=%s" % (self.hs.config.acme_port, host)
+            )
+            listeners.append(endpoint.listen(srv))
+
+        # Make sure we are registered to the ACME server. There's no public API
+        # for this, it is usually triggered by startService, but since we don't
+        # want it to control where we save the certificates, we have to reach in
+        # and trigger the registration machinery ourselves.
+        self._issuer._registered = False
+        yield self._issuer._ensure_registered()
+
+        # Return a Deferred that will fire when all the servers have started up.
+        yield defer.DeferredList(listeners, fireOnOneErrback=True, consumeErrors=True)
+
+    @defer.inlineCallbacks
+    def provision_certificate(self):
+
+        logger.warning("Reprovisioning %s", self.hs.hostname)
+
+        try:
+            yield self._issuer.issue_cert(self.hs.hostname)
+        except Exception:
+            logger.exception("Fail!")
+            raise
+        logger.warning("Reprovisioned %s, saving.", self.hs.hostname)
+        cert_chain = self._store.certs[self.hs.hostname]
+
+        try:
+            with open(self.hs.config.tls_private_key_file, "wb") as private_key_file:
+                for x in cert_chain:
+                    if x.startswith(b"-----BEGIN RSA PRIVATE KEY-----"):
+                        private_key_file.write(x)
+
+            with open(self.hs.config.tls_certificate_file, "wb") as certificate_file:
+                for x in cert_chain:
+                    if x.startswith(b"-----BEGIN CERTIFICATE-----"):
+                        certificate_file.write(x)
+        except Exception:
+            logger.exception("Failed saving!")
+            raise
+
+        defer.returnValue(True)
diff --git a/synapse/handlers/room_list.py b/synapse/handlers/room_list.py
index dc88620885..13e212d669 100644
--- a/synapse/handlers/room_list.py
+++ b/synapse/handlers/room_list.py
@@ -73,8 +73,14 @@ class RoomListHandler(BaseHandler):
             # We explicitly don't bother caching searches or requests for
             # appservice specific lists.
             logger.info("Bypassing cache as search request.")
+
+            # XXX: Quick hack to stop room directory queries taking too long.
+            # Timeout request after 60s. Probably want a more fundamental
+            # solution at some point
+            timeout = self.clock.time() + 60
             return self._get_public_room_list(
-                limit, since_token, search_filter, network_tuple=network_tuple,
+                limit, since_token, search_filter,
+                network_tuple=network_tuple, timeout=timeout,
             )
 
         key = (limit, since_token, network_tuple)
@@ -87,7 +93,8 @@ class RoomListHandler(BaseHandler):
     @defer.inlineCallbacks
     def _get_public_room_list(self, limit=None, since_token=None,
                               search_filter=None,
-                              network_tuple=EMPTY_THIRD_PARTY_ID,):
+                              network_tuple=EMPTY_THIRD_PARTY_ID,
+                              timeout=None,):
         if since_token and since_token != "END":
             since_token = RoomListNextBatch.from_token(since_token)
         else:
@@ -202,6 +209,9 @@ class RoomListHandler(BaseHandler):
 
         chunk = []
         for i in range(0, len(rooms_to_scan), step):
+            if timeout and self.clock.time() > timeout:
+                raise Exception("Timed out searching room directory")
+
             batch = rooms_to_scan[i:i + step]
             logger.info("Processing %i rooms for result", len(batch))
             yield concurrently_execute(
diff --git a/synapse/handlers/user_directory.py b/synapse/handlers/user_directory.py
index 3c40999338..120815b09b 100644
--- a/synapse/handlers/user_directory.py
+++ b/synapse/handlers/user_directory.py
@@ -19,6 +19,7 @@ from six import iteritems
 
 from twisted.internet import defer
 
+import synapse.metrics
 from synapse.api.constants import EventTypes, JoinRules, Membership
 from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.roommember import ProfileInfo
@@ -163,6 +164,11 @@ class UserDirectoryHandler(object):
                 yield self._handle_deltas(deltas)
 
                 self.pos = deltas[-1]["stream_id"]
+
+                # Expose current event processing position to prometheus
+                synapse.metrics.event_processing_positions.labels(
+                    "user_dir").set(self.pos)
+
                 yield self.store.update_user_directory_stream_pos(self.pos)
 
     @defer.inlineCallbacks
diff --git a/synapse/http/client.py b/synapse/http/client.py
index afcf698b29..47a1f82ff0 100644
--- a/synapse/http/client.py
+++ b/synapse/http/client.py
@@ -333,9 +333,10 @@ class SimpleHttpClient(object):
             "POST", uri, headers=Headers(actual_headers), data=query_bytes
         )
 
+        body = yield make_deferred_yieldable(readBody(response))
+
         if 200 <= response.code < 300:
-            body = yield make_deferred_yieldable(treq.json_content(response))
-            defer.returnValue(body)
+            defer.returnValue(json.loads(body))
         else:
             raise HttpResponseException(response.code, response.phrase, body)
 
diff --git a/synapse/http/endpoint.py b/synapse/http/endpoint.py
index 815f8ff2f7..cd79ebab62 100644
--- a/synapse/http/endpoint.py
+++ b/synapse/http/endpoint.py
@@ -13,15 +13,8 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import logging
-import random
 import re
 
-from twisted.internet import defer
-from twisted.internet.endpoints import HostnameEndpoint, wrapClientTLS
-from twisted.internet.error import ConnectError
-
-from synapse.http.federation.srv_resolver import Server, resolve_service
-
 logger = logging.getLogger(__name__)
 
 
@@ -88,140 +81,3 @@ def parse_and_validate_server_name(server_name):
         ))
 
     return host, port
-
-
-def matrix_federation_endpoint(reactor, destination, tls_client_options_factory=None,
-                               timeout=None):
-    """Construct an endpoint for the given matrix destination.
-
-    Args:
-        reactor: Twisted reactor.
-        destination (unicode): The name of the server to connect to.
-        tls_client_options_factory
-            (synapse.crypto.context_factory.ClientTLSOptionsFactory):
-            Factory which generates TLS options for client connections.
-        timeout (int): connection timeout in seconds
-    """
-
-    domain, port = parse_server_name(destination)
-
-    endpoint_kw_args = {}
-
-    if timeout is not None:
-        endpoint_kw_args.update(timeout=timeout)
-
-    if tls_client_options_factory is None:
-        transport_endpoint = HostnameEndpoint
-        default_port = 8008
-    else:
-        # the SNI string should be the same as the Host header, minus the port.
-        # as per https://github.com/matrix-org/synapse/issues/2525#issuecomment-336896777,
-        # the Host header and SNI should therefore be the server_name of the remote
-        # server.
-        tls_options = tls_client_options_factory.get_options(domain)
-
-        def transport_endpoint(reactor, host, port, timeout):
-            return wrapClientTLS(
-                tls_options,
-                HostnameEndpoint(reactor, host, port, timeout=timeout),
-            )
-        default_port = 8448
-
-    if port is None:
-        return SRVClientEndpoint(
-            reactor, "matrix", domain, protocol="tcp",
-            default_port=default_port, endpoint=transport_endpoint,
-            endpoint_kw_args=endpoint_kw_args
-        )
-    else:
-        return transport_endpoint(
-            reactor, domain, port, **endpoint_kw_args
-        )
-
-
-class SRVClientEndpoint(object):
-    """An endpoint which looks up SRV records for a service.
-    Cycles through the list of servers starting with each call to connect
-    picking the next server.
-    Implements twisted.internet.interfaces.IStreamClientEndpoint.
-    """
-
-    def __init__(self, reactor, service, domain, protocol="tcp",
-                 default_port=None, endpoint=HostnameEndpoint,
-                 endpoint_kw_args={}):
-        self.reactor = reactor
-        self.service_name = "_%s._%s.%s" % (service, protocol, domain)
-
-        if default_port is not None:
-            self.default_server = Server(
-                host=domain,
-                port=default_port,
-            )
-        else:
-            self.default_server = None
-
-        self.endpoint = endpoint
-        self.endpoint_kw_args = endpoint_kw_args
-
-        self.servers = None
-        self.used_servers = None
-
-    @defer.inlineCallbacks
-    def fetch_servers(self):
-        self.used_servers = []
-        self.servers = yield resolve_service(self.service_name)
-
-    def pick_server(self):
-        if not self.servers:
-            if self.used_servers:
-                self.servers = self.used_servers
-                self.used_servers = []
-                self.servers.sort()
-            elif self.default_server:
-                return self.default_server
-            else:
-                raise ConnectError(
-                    "No server available for %s" % self.service_name
-                )
-
-        # look for all servers with the same priority
-        min_priority = self.servers[0].priority
-        weight_indexes = list(
-            (index, server.weight + 1)
-            for index, server in enumerate(self.servers)
-            if server.priority == min_priority
-        )
-
-        total_weight = sum(weight for index, weight in weight_indexes)
-        target_weight = random.randint(0, total_weight)
-        for index, weight in weight_indexes:
-            target_weight -= weight
-            if target_weight <= 0:
-                server = self.servers[index]
-                # XXX: this looks totally dubious:
-                #
-                # (a) we never reuse a server until we have been through
-                #     all of the servers at the same priority, so if the
-                #     weights are A: 100, B:1, we always do ABABAB instead of
-                #     AAAA...AAAB (approximately).
-                #
-                # (b) After using all the servers at the lowest priority,
-                #     we move onto the next priority. We should only use the
-                #     second priority if servers at the top priority are
-                #     unreachable.
-                #
-                del self.servers[index]
-                self.used_servers.append(server)
-                return server
-
-    @defer.inlineCallbacks
-    def connect(self, protocolFactory):
-        if self.servers is None:
-            yield self.fetch_servers()
-        server = self.pick_server()
-        logger.info("Connecting to %s:%s", server.host, server.port)
-        endpoint = self.endpoint(
-            self.reactor, server.host, server.port, **self.endpoint_kw_args
-        )
-        connection = yield endpoint.connect(protocolFactory)
-        defer.returnValue(connection)
diff --git a/synapse/http/federation/matrix_federation_agent.py b/synapse/http/federation/matrix_federation_agent.py
new file mode 100644
index 0000000000..0ec28c6696
--- /dev/null
+++ b/synapse/http/federation/matrix_federation_agent.py
@@ -0,0 +1,125 @@
+# -*- coding: utf-8 -*-
+# Copyright 2019 New Vector Ltd
+#
+# 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 logging
+
+from zope.interface import implementer
+
+from twisted.internet import defer
+from twisted.internet.endpoints import HostnameEndpoint, wrapClientTLS
+from twisted.web.client import URI, Agent, HTTPConnectionPool
+from twisted.web.iweb import IAgent
+
+from synapse.http.endpoint import parse_server_name
+from synapse.http.federation.srv_resolver import SrvResolver, pick_server_from_list
+from synapse.util.logcontext import make_deferred_yieldable
+
+logger = logging.getLogger(__name__)
+
+
+@implementer(IAgent)
+class MatrixFederationAgent(object):
+    """An Agent-like thing which provides a `request` method which will look up a matrix
+    server and send an HTTP request to it.
+
+    Doesn't implement any retries. (Those are done in MatrixFederationHttpClient.)
+
+    Args:
+        reactor (IReactor): twisted reactor to use for underlying requests
+
+        tls_client_options_factory (ClientTLSOptionsFactory|None):
+            factory to use for fetching client tls options, or none to disable TLS.
+
+        srv_resolver (SrvResolver|None):
+            SRVResolver impl to use for looking up SRV records. None to use a default
+            implementation.
+    """
+
+    def __init__(
+        self, reactor, tls_client_options_factory, _srv_resolver=None,
+    ):
+        self._reactor = reactor
+        self._tls_client_options_factory = tls_client_options_factory
+        if _srv_resolver is None:
+            _srv_resolver = SrvResolver()
+        self._srv_resolver = _srv_resolver
+
+        self._pool = HTTPConnectionPool(reactor)
+        self._pool.retryAutomatically = False
+        self._pool.maxPersistentPerHost = 5
+        self._pool.cachedConnectionTimeout = 2 * 60
+
+    @defer.inlineCallbacks
+    def request(self, method, uri, headers=None, bodyProducer=None):
+        """
+        Args:
+            method (bytes): HTTP method: GET/POST/etc
+
+            uri (bytes): Absolute URI to be retrieved
+
+            headers (twisted.web.http_headers.Headers|None):
+                HTTP headers to send with the request, or None to
+                send no extra headers.
+
+            bodyProducer (twisted.web.iweb.IBodyProducer|None):
+                An object which can generate bytes to make up the
+                body of this request (for example, the properly encoded contents of
+                a file for a file upload).  Or None if the request is to have
+                no body.
+
+        Returns:
+            Deferred[twisted.web.iweb.IResponse]:
+                fires when the header of the response has been received (regardless of the
+                response status code). Fails if there is any problem which prevents that
+                response from being received (including problems that prevent the request
+                from being sent).
+        """
+
+        parsed_uri = URI.fromBytes(uri)
+        server_name_bytes = parsed_uri.netloc
+        host, port = parse_server_name(server_name_bytes.decode("ascii"))
+
+        # XXX disabling TLS is really only supported here for the benefit of the
+        # unit tests. We should make the UTs cope with TLS rather than having to make
+        # the code support the unit tests.
+        if self._tls_client_options_factory is None:
+            tls_options = None
+        else:
+            tls_options = self._tls_client_options_factory.get_options(host)
+
+        if port is not None:
+            target = (host, port)
+        else:
+            service_name = b"_matrix._tcp.%s" % (server_name_bytes, )
+            server_list = yield self._srv_resolver.resolve_service(service_name)
+            if not server_list:
+                target = (host, 8448)
+                logger.debug("No SRV record for %s, using %s", host, target)
+            else:
+                target = pick_server_from_list(server_list)
+
+        class EndpointFactory(object):
+            @staticmethod
+            def endpointForURI(_uri):
+                logger.info("Connecting to %s:%s", target[0], target[1])
+                ep = HostnameEndpoint(self._reactor, host=target[0], port=target[1])
+                if tls_options is not None:
+                    ep = wrapClientTLS(tls_options, ep)
+                return ep
+
+        agent = Agent.usingEndpointFactory(self._reactor, EndpointFactory(), self._pool)
+        res = yield make_deferred_yieldable(
+            agent.request(method, uri, headers, bodyProducer)
+        )
+        defer.returnValue(res)
diff --git a/synapse/http/federation/srv_resolver.py b/synapse/http/federation/srv_resolver.py
index c49b82c394..71830c549d 100644
--- a/synapse/http/federation/srv_resolver.py
+++ b/synapse/http/federation/srv_resolver.py
@@ -15,6 +15,7 @@
 # limitations under the License.
 
 import logging
+import random
 import time
 
 import attr
@@ -51,74 +52,118 @@ class Server(object):
     expires = attr.ib(default=0)
 
 
-@defer.inlineCallbacks
-def resolve_service(service_name, dns_client=client, cache=SERVER_CACHE, clock=time):
-    """Look up a SRV record, with caching
+def pick_server_from_list(server_list):
+    """Randomly choose a server from the server list
+
+    Args:
+        server_list (list[Server]): list of candidate servers
+
+    Returns:
+        Tuple[bytes, int]: (host, port) pair for the chosen server
+    """
+    if not server_list:
+        raise RuntimeError("pick_server_from_list called with empty list")
+
+    # TODO: currently we only use the lowest-priority servers. We should maintain a
+    # cache of servers known to be "down" and filter them out
+
+    min_priority = min(s.priority for s in server_list)
+    eligible_servers = list(s for s in server_list if s.priority == min_priority)
+    total_weight = sum(s.weight for s in eligible_servers)
+    target_weight = random.randint(0, total_weight)
+
+    for s in eligible_servers:
+        target_weight -= s.weight
+
+        if target_weight <= 0:
+            return s.host, s.port
+
+    # this should be impossible.
+    raise RuntimeError(
+        "pick_server_from_list got to end of eligible server list.",
+    )
+
+
+class SrvResolver(object):
+    """Interface to the dns client to do SRV lookups, with result caching.
 
     The default resolver in twisted.names doesn't do any caching (it has a CacheResolver,
     but the cache never gets populated), so we add our own caching layer here.
 
     Args:
-        service_name (unicode|bytes): record to look up
         dns_client (twisted.internet.interfaces.IResolver): twisted resolver impl
         cache (dict): cache object
-        clock (object): clock implementation. must provide a time() method.
-
-    Returns:
-        Deferred[list[Server]]: a list of the SRV records, or an empty list if none found
+        get_time (callable): clock implementation. Should return seconds since the epoch
     """
-    # TODO: the dns client handles both unicode names (encoding via idna) and pre-encoded
-    # byteses; however they will obviously end up as separate entries in the cache. We
-    # should pick one form and stick with it.
-    cache_entry = cache.get(service_name, None)
-    if cache_entry:
-        if all(s.expires > int(clock.time()) for s in cache_entry):
-            servers = list(cache_entry)
-            defer.returnValue(servers)
-
-    try:
-        answers, _, _ = yield make_deferred_yieldable(
-            dns_client.lookupService(service_name),
-        )
-    except DNSNameError:
-        # TODO: cache this. We can get the SOA out of the exception, and use
-        # the negative-TTL value.
-        defer.returnValue([])
-    except DomainError as e:
-        # We failed to resolve the name (other than a NameError)
-        # Try something in the cache, else rereaise
-        cache_entry = cache.get(service_name, None)
+    def __init__(self, dns_client=client, cache=SERVER_CACHE, get_time=time.time):
+        self._dns_client = dns_client
+        self._cache = cache
+        self._get_time = get_time
+
+    @defer.inlineCallbacks
+    def resolve_service(self, service_name):
+        """Look up a SRV record
+
+        Args:
+            service_name (bytes): record to look up
+
+        Returns:
+            Deferred[list[Server]]:
+                a list of the SRV records, or an empty list if none found
+        """
+        now = int(self._get_time())
+
+        if not isinstance(service_name, bytes):
+            raise TypeError("%r is not a byte string" % (service_name,))
+
+        cache_entry = self._cache.get(service_name, None)
         if cache_entry:
-            logger.warn(
-                "Failed to resolve %r, falling back to cache. %r",
-                service_name, e
+            if all(s.expires > now for s in cache_entry):
+                servers = list(cache_entry)
+                defer.returnValue(servers)
+
+        try:
+            answers, _, _ = yield make_deferred_yieldable(
+                self._dns_client.lookupService(service_name),
             )
-            defer.returnValue(list(cache_entry))
-        else:
-            raise e
-
-    if (len(answers) == 1
-            and answers[0].type == dns.SRV
-            and answers[0].payload
-            and answers[0].payload.target == dns.Name(b'.')):
-        raise ConnectError("Service %s unavailable" % service_name)
-
-    servers = []
-
-    for answer in answers:
-        if answer.type != dns.SRV or not answer.payload:
-            continue
-
-        payload = answer.payload
-
-        servers.append(Server(
-            host=payload.target.name,
-            port=payload.port,
-            priority=payload.priority,
-            weight=payload.weight,
-            expires=int(clock.time()) + answer.ttl,
-        ))
-
-    servers.sort()  # FIXME: get rid of this (it's broken by the attrs change)
-    cache[service_name] = list(servers)
-    defer.returnValue(servers)
+        except DNSNameError:
+            # TODO: cache this. We can get the SOA out of the exception, and use
+            # the negative-TTL value.
+            defer.returnValue([])
+        except DomainError as e:
+            # We failed to resolve the name (other than a NameError)
+            # Try something in the cache, else rereaise
+            cache_entry = self._cache.get(service_name, None)
+            if cache_entry:
+                logger.warn(
+                    "Failed to resolve %r, falling back to cache. %r",
+                    service_name, e
+                )
+                defer.returnValue(list(cache_entry))
+            else:
+                raise e
+
+        if (len(answers) == 1
+                and answers[0].type == dns.SRV
+                and answers[0].payload
+                and answers[0].payload.target == dns.Name(b'.')):
+            raise ConnectError("Service %s unavailable" % service_name)
+
+        servers = []
+
+        for answer in answers:
+            if answer.type != dns.SRV or not answer.payload:
+                continue
+
+            payload = answer.payload
+
+            servers.append(Server(
+                host=payload.target.name,
+                port=payload.port,
+                priority=payload.priority,
+                weight=payload.weight,
+                expires=now + answer.ttl,
+            ))
+
+        self._cache[service_name] = list(servers)
+        defer.returnValue(servers)
diff --git a/synapse/http/matrixfederationclient.py b/synapse/http/matrixfederationclient.py
index 250bb1ef91..980e912348 100644
--- a/synapse/http/matrixfederationclient.py
+++ b/synapse/http/matrixfederationclient.py
@@ -32,7 +32,7 @@ from twisted.internet import defer, protocol
 from twisted.internet.error import DNSLookupError
 from twisted.internet.task import _EPSILON, Cooperator
 from twisted.web._newclient import ResponseDone
-from twisted.web.client import Agent, FileBodyProducer, HTTPConnectionPool
+from twisted.web.client import FileBodyProducer
 from twisted.web.http_headers import Headers
 
 import synapse.metrics
@@ -44,7 +44,7 @@ from synapse.api.errors import (
     RequestSendFailed,
     SynapseError,
 )
-from synapse.http.endpoint import matrix_federation_endpoint
+from synapse.http.federation.matrix_federation_agent import MatrixFederationAgent
 from synapse.util.async_helpers import timeout_deferred
 from synapse.util.logcontext import make_deferred_yieldable
 from synapse.util.metrics import Measure
@@ -66,20 +66,6 @@ else:
     MAXINT = sys.maxint
 
 
-class MatrixFederationEndpointFactory(object):
-    def __init__(self, hs):
-        self.reactor = hs.get_reactor()
-        self.tls_client_options_factory = hs.tls_client_options_factory
-
-    def endpointForURI(self, uri):
-        destination = uri.netloc.decode('ascii')
-
-        return matrix_federation_endpoint(
-            self.reactor, destination, timeout=10,
-            tls_client_options_factory=self.tls_client_options_factory
-        )
-
-
 _next_id = 1
 
 
@@ -187,12 +173,10 @@ class MatrixFederationHttpClient(object):
         self.signing_key = hs.config.signing_key[0]
         self.server_name = hs.hostname
         reactor = hs.get_reactor()
-        pool = HTTPConnectionPool(reactor)
-        pool.retryAutomatically = False
-        pool.maxPersistentPerHost = 5
-        pool.cachedConnectionTimeout = 2 * 60
-        self.agent = Agent.usingEndpointFactory(
-            reactor, MatrixFederationEndpointFactory(hs), pool=pool
+
+        self.agent = MatrixFederationAgent(
+            hs.get_reactor(),
+            hs.tls_client_options_factory,
         )
         self.clock = hs.get_clock()
         self._store = hs.get_datastore()
@@ -316,9 +300,9 @@ class MatrixFederationHttpClient(object):
                     headers_dict[b"Authorization"] = auth_headers
 
                     logger.info(
-                        "{%s} [%s] Sending request: %s %s",
+                        "{%s} [%s] Sending request: %s %s; timeout %fs",
                         request.txn_id, request.destination, request.method,
-                        url_str,
+                        url_str, _sec_timeout,
                     )
 
                     try:
@@ -338,12 +322,11 @@ class MatrixFederationHttpClient(object):
                                 reactor=self.hs.get_reactor(),
                             )
 
-                            response = yield make_deferred_yieldable(
-                                request_deferred,
-                            )
+                            response = yield request_deferred
                     except DNSLookupError as e:
                         raise_from(RequestSendFailed(e, can_retry=retry_on_dns_fail), e)
                     except Exception as e:
+                        logger.info("Failed to send request: %s", e)
                         raise_from(RequestSendFailed(e, can_retry=True), e)
 
                     logger.info(
diff --git a/synapse/python_dependencies.py b/synapse/python_dependencies.py
index 882e844eb1..756721e304 100644
--- a/synapse/python_dependencies.py
+++ b/synapse/python_dependencies.py
@@ -79,6 +79,10 @@ CONDITIONAL_REQUIREMENTS = {
     # ConsentResource uses select_autoescape, which arrived in jinja 2.9
     "resources.consent": ["Jinja2>=2.9"],
 
+    # ACME support is required to provision TLS certificates from authorities
+    # that use the protocol, such as Let's Encrypt.
+    "acme": ["txacme>=0.9.2"],
+
     "saml2": ["pysaml2>=4.5.0"],
     "url_preview": ["lxml>=3.5.0"],
     "test": ["mock>=2.0"],
diff --git a/synapse/rest/client/v2_alpha/register.py b/synapse/rest/client/v2_alpha/register.py
index 14025cd219..7f812b8209 100644
--- a/synapse/rest/client/v2_alpha/register.py
+++ b/synapse/rest/client/v2_alpha/register.py
@@ -416,8 +416,11 @@ class RegisterRestServlet(RestServlet):
             )
             # Necessary due to auth checks prior to the threepid being
             # written to the db
-            if is_threepid_reserved(self.hs.config, threepid):
-                yield self.store.upsert_monthly_active_user(registered_user_id)
+            if threepid:
+                if is_threepid_reserved(
+                    self.hs.config.mau_limits_reserved_threepids, threepid
+                ):
+                    yield self.store.upsert_monthly_active_user(registered_user_id)
 
             # remember that we've now registered that user account, and with
             #  what user ID (since the user may not have specified)
diff --git a/synapse/server.py b/synapse/server.py
index 9985687b95..c8914302cf 100644
--- a/synapse/server.py
+++ b/synapse/server.py
@@ -46,6 +46,7 @@ from synapse.federation.transport.client import TransportLayerClient
 from synapse.groups.attestations import GroupAttestationSigning, GroupAttestionRenewer
 from synapse.groups.groups_server import GroupsServerHandler
 from synapse.handlers import Handlers
+from synapse.handlers.acme import AcmeHandler
 from synapse.handlers.appservice import ApplicationServicesHandler
 from synapse.handlers.auth import AuthHandler, MacaroonGenerator
 from synapse.handlers.deactivate_account import DeactivateAccountHandler
@@ -129,6 +130,7 @@ class HomeServer(object):
         'sync_handler',
         'typing_handler',
         'room_list_handler',
+        'acme_handler',
         'auth_handler',
         'device_handler',
         'e2e_keys_handler',
@@ -310,6 +312,9 @@ class HomeServer(object):
     def build_e2e_room_keys_handler(self):
         return E2eRoomKeysHandler(self)
 
+    def build_acme_handler(self):
+        return AcmeHandler(self)
+
     def build_application_service_api(self):
         return ApplicationServiceApi(self)
 
diff --git a/synapse/storage/_base.py b/synapse/storage/_base.py
index 865b5e915a..f62f70b9f1 100644
--- a/synapse/storage/_base.py
+++ b/synapse/storage/_base.py
@@ -26,6 +26,7 @@ from prometheus_client import Histogram
 from twisted.internet import defer
 
 from synapse.api.errors import StoreError
+from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.engines import PostgresEngine
 from synapse.util.caches.descriptors import Cache
 from synapse.util.logcontext import LoggingContext, PreserveLoggingContext
@@ -192,6 +193,51 @@ class SQLBaseStore(object):
 
         self.database_engine = hs.database_engine
 
+        # A set of tables that are not safe to use native upserts in.
+        self._unsafe_to_upsert_tables = {"user_ips"}
+
+        if self.database_engine.can_native_upsert:
+            # Check ASAP (and then later, every 1s) to see if we have finished
+            # background updates of tables that aren't safe to update.
+            self._clock.call_later(
+                0.0,
+                run_as_background_process,
+                "upsert_safety_check",
+                self._check_safe_to_upsert
+            )
+
+    @defer.inlineCallbacks
+    def _check_safe_to_upsert(self):
+        """
+        Is it safe to use native UPSERT?
+
+        If there are background updates, we will need to wait, as they may be
+        the addition of indexes that set the UNIQUE constraint that we require.
+
+        If the background updates have not completed, wait 15 sec and check again.
+        """
+        updates = yield self._simple_select_list(
+            "background_updates",
+            keyvalues=None,
+            retcols=["update_name"],
+            desc="check_background_updates",
+        )
+        updates = [x["update_name"] for x in updates]
+
+        # The User IPs table in schema #53 was missing a unique index, which we
+        # run as a background update.
+        if "user_ips_device_unique_index" not in updates:
+            self._unsafe_to_upsert_tables.discard("user_ips")
+
+        # If there's any tables left to check, reschedule to run.
+        if self._unsafe_to_upsert_tables:
+            self._clock.call_later(
+                15.0,
+                run_as_background_process,
+                "upsert_safety_check",
+                self._check_safe_to_upsert
+            )
+
     def start_profiling(self):
         self._previous_loop_ts = self._clock.time_msec()
 
@@ -494,8 +540,15 @@ class SQLBaseStore(object):
         txn.executemany(sql, vals)
 
     @defer.inlineCallbacks
-    def _simple_upsert(self, table, keyvalues, values,
-                       insertion_values={}, desc="_simple_upsert", lock=True):
+    def _simple_upsert(
+        self,
+        table,
+        keyvalues,
+        values,
+        insertion_values={},
+        desc="_simple_upsert",
+        lock=True
+    ):
         """
 
         `lock` should generally be set to True (the default), but can be set
@@ -516,16 +569,21 @@ class SQLBaseStore(object):
                 inserting
             lock (bool): True to lock the table when doing the upsert.
         Returns:
-            Deferred(bool): True if a new entry was created, False if an
-                existing one was updated.
+            Deferred(None or bool): Native upserts always return None. Emulated
+            upserts return True if a new entry was created, False if an existing
+            one was updated.
         """
         attempts = 0
         while True:
             try:
                 result = yield self.runInteraction(
                     desc,
-                    self._simple_upsert_txn, table, keyvalues, values, insertion_values,
-                    lock=lock
+                    self._simple_upsert_txn,
+                    table,
+                    keyvalues,
+                    values,
+                    insertion_values,
+                    lock=lock,
                 )
                 defer.returnValue(result)
             except self.database_engine.module.IntegrityError as e:
@@ -537,12 +595,71 @@ class SQLBaseStore(object):
 
                 # presumably we raced with another transaction: let's retry.
                 logger.warn(
-                    "IntegrityError when upserting into %s; retrying: %s",
-                    table, e
+                    "%s when upserting into %s; retrying: %s", e.__name__, table, e
                 )
 
-    def _simple_upsert_txn(self, txn, table, keyvalues, values, insertion_values={},
-                           lock=True):
+    def _simple_upsert_txn(
+        self,
+        txn,
+        table,
+        keyvalues,
+        values,
+        insertion_values={},
+        lock=True,
+    ):
+        """
+        Pick the UPSERT method which works best on the platform. Either the
+        native one (Pg9.5+, recent SQLites), or fall back to an emulated method.
+
+        Args:
+            txn: The transaction to use.
+            table (str): The table to upsert into
+            keyvalues (dict): The unique key tables and their new values
+            values (dict): The nonunique columns and their new values
+            insertion_values (dict): additional key/values to use only when
+                inserting
+            lock (bool): True to lock the table when doing the upsert.
+        Returns:
+            None or bool: Native upserts always return None. Emulated
+            upserts return True if a new entry was created, False if an existing
+            one was updated.
+        """
+        if (
+            self.database_engine.can_native_upsert
+            and table not in self._unsafe_to_upsert_tables
+        ):
+            return self._simple_upsert_txn_native_upsert(
+                txn,
+                table,
+                keyvalues,
+                values,
+                insertion_values=insertion_values,
+            )
+        else:
+            return self._simple_upsert_txn_emulated(
+                txn,
+                table,
+                keyvalues,
+                values,
+                insertion_values=insertion_values,
+                lock=lock,
+            )
+
+    def _simple_upsert_txn_emulated(
+        self, txn, table, keyvalues, values, insertion_values={}, lock=True
+    ):
+        """
+        Args:
+            table (str): The table to upsert into
+            keyvalues (dict): The unique key tables and their new values
+            values (dict): The nonunique columns and their new values
+            insertion_values (dict): additional key/values to use only when
+                inserting
+            lock (bool): True to lock the table when doing the upsert.
+        Returns:
+            bool: Return True if a new entry was created, False if an existing
+            one was updated.
+        """
         # We need to lock the table :(, unless we're *really* careful
         if lock:
             self.database_engine.lock_table(txn, table)
@@ -577,12 +694,44 @@ class SQLBaseStore(object):
         sql = "INSERT INTO %s (%s) VALUES (%s)" % (
             table,
             ", ".join(k for k in allvalues),
-            ", ".join("?" for _ in allvalues)
+            ", ".join("?" for _ in allvalues),
         )
         txn.execute(sql, list(allvalues.values()))
         # successfully inserted
         return True
 
+    def _simple_upsert_txn_native_upsert(
+        self, txn, table, keyvalues, values, insertion_values={}
+    ):
+        """
+        Use the native UPSERT functionality in recent PostgreSQL versions.
+
+        Args:
+            table (str): The table to upsert into
+            keyvalues (dict): The unique key tables and their new values
+            values (dict): The nonunique columns and their new values
+            insertion_values (dict): additional key/values to use only when
+                inserting
+        Returns:
+            None
+        """
+        allvalues = {}
+        allvalues.update(keyvalues)
+        allvalues.update(values)
+        allvalues.update(insertion_values)
+
+        sql = (
+            "INSERT INTO %s (%s) VALUES (%s) "
+            "ON CONFLICT (%s) DO UPDATE SET %s"
+        ) % (
+            table,
+            ", ".join(k for k in allvalues),
+            ", ".join("?" for _ in allvalues),
+            ", ".join(k for k in keyvalues),
+            ", ".join(k + "=EXCLUDED." + k for k in values),
+        )
+        txn.execute(sql, list(allvalues.values()))
+
     def _simple_select_one(self, table, keyvalues, retcols,
                            allow_none=False, desc="_simple_select_one"):
         """Executes a SELECT query on the named table, which is expected to
diff --git a/synapse/storage/client_ips.py b/synapse/storage/client_ips.py
index 78721a941a..091d7116c5 100644
--- a/synapse/storage/client_ips.py
+++ b/synapse/storage/client_ips.py
@@ -143,6 +143,11 @@ class ClientIpStore(background_updates.BackgroundUpdateStore):
         # If it returns None, then we're processing the last batch
         last = end_last_seen is None
 
+        logger.info(
+            "Scanning for duplicate 'user_ips' rows in range: %s <= last_seen < %s",
+            begin_last_seen, end_last_seen,
+        )
+
         def remove(txn):
             # This works by looking at all entries in the given time span, and
             # then for each (user_id, access_token, ip) tuple in that range
@@ -170,7 +175,6 @@ class ClientIpStore(background_updates.BackgroundUpdateStore):
                     SELECT user_id, access_token, ip
                     FROM user_ips
                     WHERE {}
-                    ORDER BY last_seen
                 ) c
                 INNER JOIN user_ips USING (user_id, access_token, ip)
                 GROUP BY user_id, access_token, ip
@@ -253,7 +257,10 @@ class ClientIpStore(background_updates.BackgroundUpdateStore):
         )
 
     def _update_client_ips_batch_txn(self, txn, to_update):
-        self.database_engine.lock_table(txn, "user_ips")
+        if "user_ips" in self._unsafe_to_upsert_tables or (
+            not self.database_engine.can_native_upsert
+        ):
+            self.database_engine.lock_table(txn, "user_ips")
 
         for entry in iteritems(to_update):
             (user_id, access_token, ip), (user_agent, device_id, last_seen) = entry
diff --git a/synapse/storage/engines/__init__.py b/synapse/storage/engines/__init__.py
index e2f9de8451..ff5ef97ca8 100644
--- a/synapse/storage/engines/__init__.py
+++ b/synapse/storage/engines/__init__.py
@@ -18,7 +18,7 @@ import platform
 
 from ._base import IncorrectDatabaseSetup
 from .postgres import PostgresEngine
-from .sqlite3 import Sqlite3Engine
+from .sqlite import Sqlite3Engine
 
 SUPPORTED_MODULE = {
     "sqlite3": Sqlite3Engine,
diff --git a/synapse/storage/engines/postgres.py b/synapse/storage/engines/postgres.py
index 42225f8a2a..4004427c7b 100644
--- a/synapse/storage/engines/postgres.py
+++ b/synapse/storage/engines/postgres.py
@@ -38,6 +38,13 @@ class PostgresEngine(object):
         return sql.replace("?", "%s")
 
     def on_new_connection(self, db_conn):
+
+        # Get the version of PostgreSQL that we're using. As per the psycopg2
+        # docs: The number is formed by converting the major, minor, and
+        # revision numbers into two-decimal-digit numbers and appending them
+        # together. For example, version 8.1.5 will be returned as 80105
+        self._version = db_conn.server_version
+
         db_conn.set_isolation_level(
             self.module.extensions.ISOLATION_LEVEL_REPEATABLE_READ
         )
@@ -54,6 +61,13 @@ class PostgresEngine(object):
 
         cursor.close()
 
+    @property
+    def can_native_upsert(self):
+        """
+        Can we use native UPSERTs? This requires PostgreSQL 9.5+.
+        """
+        return self._version >= 90500
+
     def is_deadlock(self, error):
         if isinstance(error, self.module.DatabaseError):
             # https://www.postgresql.org/docs/current/static/errcodes-appendix.html
diff --git a/synapse/storage/engines/sqlite3.py b/synapse/storage/engines/sqlite.py
index 19949fc474..c64d73ff21 100644
--- a/synapse/storage/engines/sqlite3.py
+++ b/synapse/storage/engines/sqlite.py
@@ -15,6 +15,7 @@
 
 import struct
 import threading
+from sqlite3 import sqlite_version_info
 
 from synapse.storage.prepare_database import prepare_database
 
@@ -30,6 +31,14 @@ class Sqlite3Engine(object):
         self._current_state_group_id = None
         self._current_state_group_id_lock = threading.Lock()
 
+    @property
+    def can_native_upsert(self):
+        """
+        Do we support native UPSERTs? This requires SQLite3 3.24+, plus some
+        more work we haven't done yet to tell what was inserted vs updated.
+        """
+        return sqlite_version_info >= (3, 24, 0)
+
     def check_database(self, txn):
         pass
 
diff --git a/synapse/storage/pusher.py b/synapse/storage/pusher.py
index 2743b52bad..134297e284 100644
--- a/synapse/storage/pusher.py
+++ b/synapse/storage/pusher.py
@@ -215,7 +215,7 @@ class PusherStore(PusherWorkerStore):
         with self._pushers_id_gen.get_next() as stream_id:
             # no need to lock because `pushers` has a unique key on
             # (app_id, pushkey, user_name) so _simple_upsert will retry
-            newly_inserted = yield self._simple_upsert(
+            yield self._simple_upsert(
                 table="pushers",
                 keyvalues={
                     "app_id": app_id,
@@ -238,7 +238,12 @@ class PusherStore(PusherWorkerStore):
                 lock=False,
             )
 
-            if newly_inserted:
+            user_has_pusher = self.get_if_user_has_pusher.cache.get(
+                (user_id,), None, update_metrics=False
+            )
+
+            if user_has_pusher is not True:
+                # invalidate, since we the user might not have had a pusher before
                 yield self.runInteraction(
                     "add_pusher",
                     self._invalidate_cache_and_stream,
diff --git a/synapse/storage/user_directory.py b/synapse/storage/user_directory.py
index a8781b0e5d..ce48212265 100644
--- a/synapse/storage/user_directory.py
+++ b/synapse/storage/user_directory.py
@@ -168,14 +168,14 @@ class UserDirectoryStore(SQLBaseStore):
             if isinstance(self.database_engine, PostgresEngine):
                 # We weight the localpart most highly, then display name and finally
                 # server name
-                if new_entry:
+                if self.database_engine.can_native_upsert:
                     sql = """
                         INSERT INTO user_directory_search(user_id, vector)
                         VALUES (?,
                             setweight(to_tsvector('english', ?), 'A')
                             || setweight(to_tsvector('english', ?), 'D')
                             || setweight(to_tsvector('english', COALESCE(?, '')), 'B')
-                        )
+                        ) ON CONFLICT (user_id) DO UPDATE SET vector=EXCLUDED.vector
                     """
                     txn.execute(
                         sql,
@@ -185,20 +185,45 @@ class UserDirectoryStore(SQLBaseStore):
                         )
                     )
                 else:
-                    sql = """
-                        UPDATE user_directory_search
-                        SET vector = setweight(to_tsvector('english', ?), 'A')
-                            || setweight(to_tsvector('english', ?), 'D')
-                            || setweight(to_tsvector('english', COALESCE(?, '')), 'B')
-                        WHERE user_id = ?
-                    """
-                    txn.execute(
-                        sql,
-                        (
-                            get_localpart_from_id(user_id), get_domain_from_id(user_id),
-                            display_name, user_id,
+                    # TODO: Remove this code after we've bumped the minimum version
+                    # of postgres to always support upserts, so we can get rid of
+                    # `new_entry` usage
+                    if new_entry is True:
+                        sql = """
+                            INSERT INTO user_directory_search(user_id, vector)
+                            VALUES (?,
+                                setweight(to_tsvector('english', ?), 'A')
+                                || setweight(to_tsvector('english', ?), 'D')
+                                || setweight(to_tsvector('english', COALESCE(?, '')), 'B')
+                            )
+                        """
+                        txn.execute(
+                            sql,
+                            (
+                                user_id, get_localpart_from_id(user_id),
+                                get_domain_from_id(user_id), display_name,
+                            )
+                        )
+                    elif new_entry is False:
+                        sql = """
+                            UPDATE user_directory_search
+                            SET vector = setweight(to_tsvector('english', ?), 'A')
+                                || setweight(to_tsvector('english', ?), 'D')
+                                || setweight(to_tsvector('english', COALESCE(?, '')), 'B')
+                            WHERE user_id = ?
+                        """
+                        txn.execute(
+                            sql,
+                            (
+                                get_localpart_from_id(user_id),
+                                get_domain_from_id(user_id),
+                                display_name, user_id,
+                            )
+                        )
+                    else:
+                        raise RuntimeError(
+                            "upsert returned None when 'can_native_upsert' is False"
                         )
-                    )
             elif isinstance(self.database_engine, Sqlite3Engine):
                 value = "%s %s" % (user_id, display_name,) if display_name else user_id
                 self._simple_upsert_txn(