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-rw-r--r--synapse/app/_base.py17
-rwxr-xr-xsynapse/app/homeserver.py5
-rw-r--r--synapse/config/_base.py9
-rw-r--r--synapse/config/homeserver.py2
-rw-r--r--synapse/config/server.py185
-rw-r--r--synapse/config/tls.py123
-rw-r--r--synapse/crypto/context_factory.py4
-rw-r--r--synapse/handlers/e2e_room_keys.py74
-rw-r--r--synapse/http/matrixfederationclient.py4
-rw-r--r--synapse/rest/client/v2_alpha/room_keys.py34
-rw-r--r--synapse/server.py6
-rw-r--r--synapse/storage/client_ips.py87
-rw-r--r--synapse/storage/e2e_room_keys.py21
-rw-r--r--synapse/storage/schema/delta/53/user_ips_index.sql10
14 files changed, 436 insertions, 145 deletions
diff --git a/synapse/app/_base.py b/synapse/app/_base.py
index 62c633146f..5b0ca312e2 100644
--- a/synapse/app/_base.py
+++ b/synapse/app/_base.py
@@ -213,16 +213,17 @@ def refresh_certificate(hs):
     Refresh the TLS certificates that Synapse is using by re-reading them from
     disk and updating the TLS context factories to use them.
     """
-    logging.info("Loading certificate from disk...")
-    hs.config.read_certificate_from_disk()
+
+    if not hs.config.has_tls_listener():
+        # attempt to reload the certs for the good of the tls_fingerprints
+        hs.config.read_certificate_from_disk(require_cert_and_key=False)
+        return
+
+    hs.config.read_certificate_from_disk(require_cert_and_key=True)
     hs.tls_server_context_factory = context_factory.ServerContextFactory(hs.config)
-    hs.tls_client_options_factory = context_factory.ClientTLSOptionsFactory(
-        hs.config
-    )
-    logging.info("Certificate loaded.")
 
     if hs._listening_services:
-        logging.info("Updating context factories...")
+        logger.info("Updating context factories...")
         for i in hs._listening_services:
             # When you listenSSL, it doesn't make an SSL port but a TCP one with
             # a TLS wrapping factory around the factory you actually want to get
@@ -237,7 +238,7 @@ def refresh_certificate(hs):
                     False,
                     i.factory.wrappedFactory
                 )
-        logging.info("Context factories updated.")
+        logger.info("Context factories updated.")
 
 
 def start(hs, listeners=None):
diff --git a/synapse/app/homeserver.py b/synapse/app/homeserver.py
index b4476bf16e..dbd98d394f 100755
--- a/synapse/app/homeserver.py
+++ b/synapse/app/homeserver.py
@@ -90,11 +90,6 @@ class SynapseHomeServer(HomeServer):
         tls = listener_config.get("tls", False)
         site_tag = listener_config.get("tag", port)
 
-        if tls and config.no_tls:
-            raise ConfigError(
-                "Listener on port %i has TLS enabled, but no_tls is set" % (port,),
-            )
-
         resources = {}
         for res in listener_config["resources"]:
             for name in res["names"]:
diff --git a/synapse/config/_base.py b/synapse/config/_base.py
index 5858fb92b4..5aec43b702 100644
--- a/synapse/config/_base.py
+++ b/synapse/config/_base.py
@@ -257,7 +257,7 @@ class Config(object):
             "--keys-directory",
             metavar="DIRECTORY",
             help="Used with 'generate-*' options to specify where files such as"
-            " certs and signing keys should be stored in, unless explicitly"
+            " signing keys should be stored, unless explicitly"
             " specified in the config.",
         )
         config_parser.add_argument(
@@ -313,16 +313,11 @@ class Config(object):
                 print(
                     (
                         "A config file has been generated in %r for server name"
-                        " %r with corresponding SSL keys and self-signed"
-                        " certificates. Please review this file and customise it"
+                        " %r. Please review this file and customise it"
                         " to your needs."
                     )
                     % (config_path, server_name)
                 )
-                print(
-                    "If this server name is incorrect, you will need to"
-                    " regenerate the SSL certificates"
-                )
                 return
             else:
                 print(
diff --git a/synapse/config/homeserver.py b/synapse/config/homeserver.py
index 5aad062c36..727fdc54d8 100644
--- a/synapse/config/homeserver.py
+++ b/synapse/config/homeserver.py
@@ -42,7 +42,7 @@ from .voip import VoipConfig
 from .workers import WorkerConfig
 
 
-class HomeServerConfig(TlsConfig, ServerConfig, DatabaseConfig, LoggingConfig,
+class HomeServerConfig(ServerConfig, TlsConfig, DatabaseConfig, LoggingConfig,
                        RatelimitConfig, ContentRepositoryConfig, CaptchaConfig,
                        VoipConfig, RegistrationConfig, MetricsConfig, ApiConfig,
                        AppServiceConfig, KeyConfig, SAML2Config, CasConfig,
diff --git a/synapse/config/server.py b/synapse/config/server.py
index f0a60cc712..c5c3aac8ed 100644
--- a/synapse/config/server.py
+++ b/synapse/config/server.py
@@ -24,6 +24,14 @@ from ._base import Config, ConfigError
 
 logger = logging.Logger(__name__)
 
+# by default, we attempt to listen on both '::' *and* '0.0.0.0' because some OSes
+# (Windows, macOS, other BSD/Linux where net.ipv6.bindv6only is set) will only listen
+# on IPv6 when '::' is set.
+#
+# We later check for errors when binding to 0.0.0.0 and ignore them if :: is also in
+# in the list.
+DEFAULT_BIND_ADDRESSES = ['::', '0.0.0.0']
+
 
 class ServerConfig(Config):
 
@@ -118,16 +126,34 @@ class ServerConfig(Config):
                 self.public_baseurl += '/'
         self.start_pushers = config.get("start_pushers", True)
 
-        self.listeners = config.get("listeners", [])
+        self.listeners = []
+        for listener in config.get("listeners", []):
+            if not isinstance(listener.get("port", None), int):
+                raise ConfigError(
+                    "Listener configuration is lacking a valid 'port' option"
+                )
+
+            if listener.setdefault("tls", False):
+                # no_tls is not really supported any more, but let's grandfather it in
+                # here.
+                if config.get("no_tls", False):
+                    logger.info(
+                        "Ignoring TLS-enabled listener on port %i due to no_tls"
+                    )
+                    continue
 
-        for listener in self.listeners:
             bind_address = listener.pop("bind_address", None)
             bind_addresses = listener.setdefault("bind_addresses", [])
 
+            # if bind_address was specified, add it to the list of addresses
             if bind_address:
                 bind_addresses.append(bind_address)
-            elif not bind_addresses:
-                bind_addresses.append('')
+
+            # if we still have an empty list of addresses, use the default list
+            if not bind_addresses:
+                bind_addresses.extend(DEFAULT_BIND_ADDRESSES)
+
+            self.listeners.append(listener)
 
         if not self.web_client_location:
             _warn_if_webclient_configured(self.listeners)
@@ -136,6 +162,9 @@ class ServerConfig(Config):
 
         bind_port = config.get("bind_port")
         if bind_port:
+            if config.get("no_tls", False):
+                raise ConfigError("no_tls is incompatible with bind_port")
+
             self.listeners = []
             bind_host = config.get("bind_host", "")
             gzip_responses = config.get("gzip_responses", True)
@@ -182,6 +211,7 @@ class ServerConfig(Config):
                 "port": manhole,
                 "bind_addresses": ["127.0.0.1"],
                 "type": "manhole",
+                "tls": False,
             })
 
         metrics_port = config.get("metrics_port")
@@ -207,6 +237,9 @@ class ServerConfig(Config):
 
         _check_resource_config(self.listeners)
 
+    def has_tls_listener(self):
+        return any(l["tls"] for l in self.listeners)
+
     def default_config(self, server_name, data_dir_path, **kwargs):
         _, bind_port = parse_and_validate_server_name(server_name)
         if bind_port is not None:
@@ -295,84 +328,106 @@ class ServerConfig(Config):
 
         # List of ports that Synapse should listen on, their purpose and their
         # configuration.
+        #
+        # Options for each listener include:
+        #
+        #   port: the TCP port to bind to
+        #
+        #   bind_addresses: a list of local addresses to listen on. The default is
+        #       'all local interfaces'.
+        #
+        #   type: the type of listener. Normally 'http', but other valid options are:
+        #       'manhole' (see docs/manhole.md),
+        #       'metrics' (see docs/metrics-howto.rst),
+        #       'replication' (see docs/workers.rst).
+        #
+        #   tls: set to true to enable TLS for this listener. Will use the TLS
+        #       key/cert specified in tls_private_key_path / tls_certificate_path.
+        #
+        #   x_forwarded: Only valid for an 'http' listener. Set to true to use the
+        #       X-Forwarded-For header as the client IP. Useful when Synapse is
+        #       behind a reverse-proxy.
+        #
+        #   resources: Only valid for an 'http' listener. A list of resources to host
+        #       on this port. Options for each resource are:
+        #
+        #       names: a list of names of HTTP resources. See below for a list of
+        #           valid resource names.
+        #
+        #       compress: set to true to enable HTTP comression for this resource.
+        #
+        #   additional_resources: Only valid for an 'http' listener. A map of
+        #        additional endpoints which should be loaded via dynamic modules.
+        #
+        # Valid resource names are:
+        #
+        #   client: the client-server API (/_matrix/client). Also implies 'media' and
+        #       'static'.
+        #
+        #   consent: user consent forms (/_matrix/consent). See
+        #       docs/consent_tracking.md.
+        #
+        #   federation: the server-server API (/_matrix/federation). Also implies
+        #       'media', 'keys', 'openid'
+        #
+        #   keys: the key discovery API (/_matrix/keys).
+        #
+        #   media: the media API (/_matrix/media).
+        #
+        #   metrics: the metrics interface. See docs/metrics-howto.rst.
+        #
+        #   openid: OpenID authentication.
+        #
+        #   replication: the HTTP replication API (/_synapse/replication). See
+        #       docs/workers.rst.
+        #
+        #   static: static resources under synapse/static (/_matrix/static). (Mostly
+        #       useful for 'fallback authentication'.)
+        #
+        #   webclient: A web client. Requires web_client_location to be set.
+        #
         listeners:
-          # Main HTTPS listener
-          # For when matrix traffic is sent directly to synapse.
-          -
-            # The port to listen for HTTPS requests on.
-            port: %(bind_port)s
-
-            # Local addresses to listen on.
-            # On Linux and Mac OS, `::` will listen on all IPv4 and IPv6
-            # addresses by default. For most other OSes, this will only listen
-            # on IPv6.
-            bind_addresses:
-              - '::'
-              - '0.0.0.0'
-
-            # This is a 'http' listener, allows us to specify 'resources'.
+          # TLS-enabled listener: for when matrix traffic is sent directly to synapse.
+          #
+          # Disabled by default. To enable it, uncomment the following. (Note that you
+          # will also need to give Synapse a TLS key and certificate: see the TLS section
+          # below.)
+          #
+          # - port: %(bind_port)s
+          #   type: http
+          #   tls: true
+          #   resources:
+          #     - names: [client, federation]
+
+          # Unsecure HTTP listener: for when matrix traffic passes through a reverse proxy
+          # that unwraps TLS.
+          #
+          # If you plan to use a reverse proxy, please see
+          # https://github.com/matrix-org/synapse/blob/master/docs/reverse_proxy.rst.
+          #
+          - port: %(unsecure_port)s
+            tls: false
+            bind_addresses: ['::1', '127.0.0.1']
             type: http
+            x_forwarded: true
 
-            tls: true
-
-            # Use the X-Forwarded-For (XFF) header as the client IP and not the
-            # actual client IP.
-            x_forwarded: false
-
-            # List of HTTP resources to serve on this listener.
             resources:
-              -
-                # List of resources to host on this listener.
-                names:
-                  - client       # The client-server APIs, both v1 and v2
-                  # - webclient  # A web client. Requires web_client_location to be set.
-
-                # Should synapse compress HTTP responses to clients that support it?
-                # This should be disabled if running synapse behind a load balancer
-                # that can do automatic compression.
-                compress: true
-
-              - names: [federation]  # Federation APIs
+              - names: [client, federation]
                 compress: false
 
-              # # If federation is disabled synapse can still expose the open ID endpoint
-              # # to allow integrations to authenticate users
-              # - names: [openid]
-              #   compress: false
-
-            # optional list of additional endpoints which can be loaded via
-            # dynamic modules
+            # example additonal_resources:
+            #
             # additional_resources:
             #   "/_matrix/my/custom/endpoint":
             #     module: my_module.CustomRequestHandler
             #     config: {}
 
-          # Unsecure HTTP listener,
-          # For when matrix traffic passes through loadbalancer that unwraps TLS.
-          - port: %(unsecure_port)s
-            tls: false
-            bind_addresses: ['::', '0.0.0.0']
-            type: http
-
-            x_forwarded: false
-
-            resources:
-              - names: [client]
-                compress: true
-              - names: [federation]
-                compress: false
-              # # If federation is disabled synapse can still expose the open ID endpoint
-              # # to allow integrations to authenticate users
-              # - names: [openid]
-              #   compress: false
-
           # Turn on the twisted ssh manhole service on localhost on the given
           # port.
           # - port: 9000
           #   bind_addresses: ['::1', '127.0.0.1']
           #   type: manhole
 
-
         # Homeserver blocking
         #
         # How to reach the server admin, used in ResourceLimitError
diff --git a/synapse/config/tls.py b/synapse/config/tls.py
index 9fcc79816d..5fb3486db1 100644
--- a/synapse/config/tls.py
+++ b/synapse/config/tls.py
@@ -23,9 +23,9 @@ from unpaddedbase64 import encode_base64
 
 from OpenSSL import crypto
 
-from synapse.config._base import Config
+from synapse.config._base import Config, ConfigError
 
-logger = logging.getLogger()
+logger = logging.getLogger(__name__)
 
 
 class TlsConfig(Config):
@@ -45,13 +45,25 @@ class TlsConfig(Config):
 
         self.tls_certificate_file = self.abspath(config.get("tls_certificate_path"))
         self.tls_private_key_file = self.abspath(config.get("tls_private_key_path"))
+
+        if self.has_tls_listener():
+            if not self.tls_certificate_file:
+                raise ConfigError(
+                    "tls_certificate_path must be specified if TLS-enabled listeners are "
+                    "configured."
+                )
+            if not self.tls_private_key_file:
+                raise ConfigError(
+                    "tls_certificate_path must be specified if TLS-enabled listeners are "
+                    "configured."
+                )
+
         self._original_tls_fingerprints = config.get("tls_fingerprints", [])
 
         if self._original_tls_fingerprints is None:
             self._original_tls_fingerprints = []
 
         self.tls_fingerprints = list(self._original_tls_fingerprints)
-        self.no_tls = config.get("no_tls", False)
 
         # This config option applies to non-federation HTTP clients
         # (e.g. for talking to recaptcha, identity servers, and such)
@@ -106,36 +118,40 @@ class TlsConfig(Config):
         days_remaining = (expires_on - now).days
         return days_remaining
 
-    def read_certificate_from_disk(self):
-        """
-        Read the certificates from disk.
+    def read_certificate_from_disk(self, require_cert_and_key):
         """
-        self.tls_certificate = self.read_tls_certificate(self.tls_certificate_file)
+        Read the certificates and private key from disk.
 
-        # Check if it is self-signed, and issue a warning if so.
-        if self.tls_certificate.get_issuer() == self.tls_certificate.get_subject():
-            warnings.warn(
-                (
-                    "Self-signed TLS certificates will not be accepted by Synapse 1.0. "
-                    "Please either provide a valid certificate, or use Synapse's ACME "
-                    "support to provision one."
+        Args:
+            require_cert_and_key (bool): set to True to throw an error if the certificate
+                and key file are not given
+        """
+        if require_cert_and_key:
+            self.tls_private_key = self.read_tls_private_key()
+            self.tls_certificate = self.read_tls_certificate()
+        elif self.tls_certificate_file:
+            # we only need the certificate for the tls_fingerprints. Reload it if we
+            # can, but it's not a fatal error if we can't.
+            try:
+                self.tls_certificate = self.read_tls_certificate()
+            except Exception as e:
+                logger.info(
+                    "Unable to read TLS certificate (%s). Ignoring as no "
+                    "tls listeners enabled.", e,
                 )
-            )
-
-        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
-        )
-        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})
+        if self.tls_certificate:
+            # 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
+            )
+            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})
 
     def default_config(self, config_dir_path, server_name, **kwargs):
         base_key_name = os.path.join(config_dir_path, server_name)
@@ -151,6 +167,8 @@ class TlsConfig(Config):
 
         return (
             """\
+        ## TLS ##
+
         # PEM-encoded X509 certificate for TLS.
         # This certificate, as of Synapse 1.0, will need to be a valid and verifiable
         # certificate, signed by a recognised Certificate Authority.
@@ -158,10 +176,10 @@ class TlsConfig(Config):
         # See 'ACME support' below to enable auto-provisioning this certificate via
         # Let's Encrypt.
         #
-        tls_certificate_path: "%(tls_certificate_path)s"
+        # tls_certificate_path: "%(tls_certificate_path)s"
 
         # PEM-encoded private key for TLS
-        tls_private_key_path: "%(tls_private_key_path)s"
+        # tls_private_key_path: "%(tls_private_key_path)s"
 
         # ACME support: This will configure Synapse to request a valid TLS certificate
         # for your configured `server_name` via Let's Encrypt.
@@ -186,7 +204,7 @@ class TlsConfig(Config):
         #
         acme:
             # ACME support is disabled by default. Uncomment the following line
-            # to enable it.
+            # (and tls_certificate_path and tls_private_key_path above) to enable it.
             #
             # enabled: true
 
@@ -211,13 +229,6 @@ class TlsConfig(Config):
             #
             # reprovision_threshold: 30
 
-        # If your server runs behind a reverse-proxy which terminates TLS connections
-        # (for both client and federation connections), it may be useful to disable
-        # All TLS support for incoming connections. Setting no_tls to True will
-        # do so (and avoid the need to give synapse a TLS private key).
-        #
-        # no_tls: True
-
         # List of allowed TLS fingerprints for this server to publish along
         # with the signing keys for this server. Other matrix servers that
         # make HTTPS requests to this server will check that the TLS
@@ -250,10 +261,38 @@ class TlsConfig(Config):
             % locals()
         )
 
-    def read_tls_certificate(self, cert_path):
-        cert_pem = self.read_file(cert_path, "tls_certificate")
-        return crypto.load_certificate(crypto.FILETYPE_PEM, cert_pem)
+    def read_tls_certificate(self):
+        """Reads the TLS certificate from the configured file, and returns it
+
+        Also checks if it is self-signed, and warns if so
+
+        Returns:
+            OpenSSL.crypto.X509: the certificate
+        """
+        cert_path = self.tls_certificate_file
+        logger.info("Loading TLS certificate from %s", cert_path)
+        cert_pem = self.read_file(cert_path, "tls_certificate_path")
+        cert = crypto.load_certificate(crypto.FILETYPE_PEM, cert_pem)
+
+        # Check if it is self-signed, and issue a warning if so.
+        if cert.get_issuer() == cert.get_subject():
+            warnings.warn(
+                (
+                    "Self-signed TLS certificates will not be accepted by Synapse 1.0. "
+                    "Please either provide a valid certificate, or use Synapse's ACME "
+                    "support to provision one."
+                )
+            )
+
+        return cert
+
+    def read_tls_private_key(self):
+        """Reads the TLS private key from the configured file, and returns it
 
-    def read_tls_private_key(self, private_key_path):
-        private_key_pem = self.read_file(private_key_path, "tls_private_key")
+        Returns:
+            OpenSSL.crypto.PKey: the private key
+        """
+        private_key_path = self.tls_private_key_file
+        logger.info("Loading TLS key from %s", private_key_path)
+        private_key_pem = self.read_file(private_key_path, "tls_private_key_path")
         return crypto.load_privatekey(crypto.FILETYPE_PEM, private_key_pem)
diff --git a/synapse/crypto/context_factory.py b/synapse/crypto/context_factory.py
index 286ad80100..85f2848fb1 100644
--- a/synapse/crypto/context_factory.py
+++ b/synapse/crypto/context_factory.py
@@ -43,9 +43,7 @@ class ServerContextFactory(ContextFactory):
             logger.exception("Failed to enable elliptic curve for TLS")
         context.set_options(SSL.OP_NO_SSLv2 | SSL.OP_NO_SSLv3)
         context.use_certificate_chain_file(config.tls_certificate_file)
-
-        if not config.no_tls:
-            context.use_privatekey(config.tls_private_key)
+        context.use_privatekey(config.tls_private_key)
 
         # https://hynek.me/articles/hardening-your-web-servers-ssl-ciphers/
         context.set_cipher_list(
diff --git a/synapse/handlers/e2e_room_keys.py b/synapse/handlers/e2e_room_keys.py
index 42b040375f..7bc174070e 100644
--- a/synapse/handlers/e2e_room_keys.py
+++ b/synapse/handlers/e2e_room_keys.py
@@ -19,7 +19,13 @@ from six import iteritems
 
 from twisted.internet import defer
 
-from synapse.api.errors import NotFoundError, RoomKeysVersionError, StoreError
+from synapse.api.errors import (
+    Codes,
+    NotFoundError,
+    RoomKeysVersionError,
+    StoreError,
+    SynapseError,
+)
 from synapse.util.async_helpers import Linearizer
 
 logger = logging.getLogger(__name__)
@@ -267,7 +273,7 @@ class E2eRoomKeysHandler(object):
             version(str): Optional; if None gives the most recent version
                 otherwise a historical one.
         Raises:
-            StoreError: code 404 if the requested backup version doesn't exist
+            NotFoundError: if the requested backup version doesn't exist
         Returns:
             A deferred of a info dict that gives the info about the new version.
 
@@ -279,7 +285,13 @@ class E2eRoomKeysHandler(object):
         """
 
         with (yield self._upload_linearizer.queue(user_id)):
-            res = yield self.store.get_e2e_room_keys_version_info(user_id, version)
+            try:
+                res = yield self.store.get_e2e_room_keys_version_info(user_id, version)
+            except StoreError as e:
+                if e.code == 404:
+                    raise NotFoundError("Unknown backup version")
+                else:
+                    raise
             defer.returnValue(res)
 
     @defer.inlineCallbacks
@@ -290,8 +302,60 @@ class E2eRoomKeysHandler(object):
             user_id(str): the user whose current backup version we're deleting
             version(str): the version id of the backup being deleted
         Raises:
-            StoreError: code 404 if this backup version doesn't exist
+            NotFoundError: if this backup version doesn't exist
         """
 
         with (yield self._upload_linearizer.queue(user_id)):
-            yield self.store.delete_e2e_room_keys_version(user_id, version)
+            try:
+                yield self.store.delete_e2e_room_keys_version(user_id, version)
+            except StoreError as e:
+                if e.code == 404:
+                    raise NotFoundError("Unknown backup version")
+                else:
+                    raise
+
+    @defer.inlineCallbacks
+    def update_version(self, user_id, version, version_info):
+        """Update the info about a given version of the user's backup
+
+        Args:
+            user_id(str): the user whose current backup version we're updating
+            version(str): the backup version we're updating
+            version_info(dict): the new information about the backup
+        Raises:
+            NotFoundError: if the requested backup version doesn't exist
+        Returns:
+            A deferred of an empty dict.
+        """
+        if "version" not in version_info:
+            raise SynapseError(
+                400,
+                "Missing version in body",
+                Codes.MISSING_PARAM
+            )
+        if version_info["version"] != version:
+            raise SynapseError(
+                400,
+                "Version in body does not match",
+                Codes.INVALID_PARAM
+            )
+        with (yield self._upload_linearizer.queue(user_id)):
+            try:
+                old_info = yield self.store.get_e2e_room_keys_version_info(
+                    user_id, version
+                )
+            except StoreError as e:
+                if e.code == 404:
+                    raise NotFoundError("Unknown backup version")
+                else:
+                    raise
+            if old_info["algorithm"] != version_info["algorithm"]:
+                raise SynapseError(
+                    400,
+                    "Algorithm does not match",
+                    Codes.INVALID_PARAM
+                )
+
+            yield self.store.update_e2e_room_keys_version(user_id, version, version_info)
+
+            defer.returnValue({})
diff --git a/synapse/http/matrixfederationclient.py b/synapse/http/matrixfederationclient.py
index 5ee4d528d2..3c24bf3805 100644
--- a/synapse/http/matrixfederationclient.py
+++ b/synapse/http/matrixfederationclient.py
@@ -168,7 +168,7 @@ class MatrixFederationHttpClient(object):
             requests.
     """
 
-    def __init__(self, hs):
+    def __init__(self, hs, tls_client_options_factory):
         self.hs = hs
         self.signing_key = hs.config.signing_key[0]
         self.server_name = hs.hostname
@@ -176,7 +176,7 @@ class MatrixFederationHttpClient(object):
 
         self.agent = MatrixFederationAgent(
             hs.get_reactor(),
-            hs.tls_client_options_factory,
+            tls_client_options_factory,
         )
         self.clock = hs.get_clock()
         self._store = hs.get_datastore()
diff --git a/synapse/rest/client/v2_alpha/room_keys.py b/synapse/rest/client/v2_alpha/room_keys.py
index ab3f1bd21a..220a0de30b 100644
--- a/synapse/rest/client/v2_alpha/room_keys.py
+++ b/synapse/rest/client/v2_alpha/room_keys.py
@@ -380,6 +380,40 @@ class RoomKeysVersionServlet(RestServlet):
         )
         defer.returnValue((200, {}))
 
+    @defer.inlineCallbacks
+    def on_PUT(self, request, version):
+        """
+        Update the information about a given version of the user's room_keys backup.
+
+        POST /room_keys/version/12345 HTTP/1.1
+        Content-Type: application/json
+        {
+            "algorithm": "m.megolm_backup.v1",
+            "auth_data": {
+                "public_key": "abcdefg",
+                "signatures": {
+                    "ed25519:something": "hijklmnop"
+                }
+            },
+            "version": "42"
+        }
+
+        HTTP/1.1 200 OK
+        Content-Type: application/json
+        {}
+        """
+        requester = yield self.auth.get_user_by_req(request, allow_guest=False)
+        user_id = requester.user.to_string()
+        info = parse_json_object_from_request(request)
+
+        if version is None:
+            raise SynapseError(400, "No version specified to update", Codes.MISSING_PARAM)
+
+        yield self.e2e_room_keys_handler.update_version(
+            user_id, version, info
+        )
+        defer.returnValue((200, {}))
+
 
 def register_servlets(hs, http_server):
     RoomKeysServlet(hs).register(http_server)
diff --git a/synapse/server.py b/synapse/server.py
index a2cf8a91cd..8615b67ad4 100644
--- a/synapse/server.py
+++ b/synapse/server.py
@@ -31,6 +31,7 @@ from synapse.api.filtering import Filtering
 from synapse.api.ratelimiting import Ratelimiter
 from synapse.appservice.api import ApplicationServiceApi
 from synapse.appservice.scheduler import ApplicationServiceScheduler
+from synapse.crypto import context_factory
 from synapse.crypto.keyring import Keyring
 from synapse.events.builder import EventBuilderFactory
 from synapse.events.spamcheck import SpamChecker
@@ -367,7 +368,10 @@ class HomeServer(object):
         return PusherPool(self)
 
     def build_http_client(self):
-        return MatrixFederationHttpClient(self)
+        tls_client_options_factory = context_factory.ClientTLSOptionsFactory(
+            self.config
+        )
+        return MatrixFederationHttpClient(self, tls_client_options_factory)
 
     def build_db_pool(self):
         name = self.db_config["name"]
diff --git a/synapse/storage/client_ips.py b/synapse/storage/client_ips.py
index 091d7116c5..9c21362226 100644
--- a/synapse/storage/client_ips.py
+++ b/synapse/storage/client_ips.py
@@ -66,6 +66,11 @@ class ClientIpStore(background_updates.BackgroundUpdateStore):
         )
 
         self.register_background_update_handler(
+            "user_ips_analyze",
+            self._analyze_user_ip,
+        )
+
+        self.register_background_update_handler(
             "user_ips_remove_dupes",
             self._remove_user_ip_dupes,
         )
@@ -109,6 +114,25 @@ class ClientIpStore(background_updates.BackgroundUpdateStore):
         defer.returnValue(1)
 
     @defer.inlineCallbacks
+    def _analyze_user_ip(self, progress, batch_size):
+        # Background update to analyze user_ips table before we run the
+        # deduplication background update. The table may not have been analyzed
+        # for ages due to the table locks.
+        #
+        # This will lock out the naive upserts to user_ips while it happens, but
+        # the analyze should be quick (28GB table takes ~10s)
+        def user_ips_analyze(txn):
+            txn.execute("ANALYZE user_ips")
+
+        yield self.runInteraction(
+            "user_ips_analyze", user_ips_analyze
+        )
+
+        yield self._end_background_update("user_ips_analyze")
+
+        defer.returnValue(1)
+
+    @defer.inlineCallbacks
     def _remove_user_ip_dupes(self, progress, batch_size):
         # This works function works by scanning the user_ips table in batches
         # based on `last_seen`. For each row in a batch it searches the rest of
@@ -167,12 +191,16 @@ class ClientIpStore(background_updates.BackgroundUpdateStore):
                 clause = "? <= last_seen AND last_seen < ?"
                 args = (begin_last_seen, end_last_seen)
 
+            # (Note: The DISTINCT in the inner query is important to ensure that
+            # the COUNT(*) is accurate, otherwise double counting may happen due
+            # to the join effectively being a cross product)
             txn.execute(
                 """
                 SELECT user_id, access_token, ip,
-                       MAX(device_id), MAX(user_agent), MAX(last_seen)
+                       MAX(device_id), MAX(user_agent), MAX(last_seen),
+                       COUNT(*)
                 FROM (
-                    SELECT user_id, access_token, ip
+                    SELECT DISTINCT user_id, access_token, ip
                     FROM user_ips
                     WHERE {}
                 ) c
@@ -186,7 +214,60 @@ class ClientIpStore(background_updates.BackgroundUpdateStore):
 
             # We've got some duplicates
             for i in res:
-                user_id, access_token, ip, device_id, user_agent, last_seen = i
+                user_id, access_token, ip, device_id, user_agent, last_seen, count = i
+
+                # We want to delete the duplicates so we end up with only a
+                # single row.
+                #
+                # The naive way of doing this would be just to delete all rows
+                # and reinsert a constructed row. However, if there are a lot of
+                # duplicate rows this can cause the table to grow a lot, which
+                # can be problematic in two ways:
+                #   1. If user_ips is already large then this can cause the
+                #      table to rapidly grow, potentially filling the disk.
+                #   2. Reinserting a lot of rows can confuse the table
+                #      statistics for postgres, causing it to not use the
+                #      correct indices for the query above, resulting in a full
+                #      table scan. This is incredibly slow for large tables and
+                #      can kill database performance. (This seems to mainly
+                #      happen for the last query where the clause is simply `? <
+                #      last_seen`)
+                #
+                # So instead we want to delete all but *one* of the duplicate
+                # rows. That is hard to do reliably, so we cheat and do a two
+                # step process:
+                #   1. Delete all rows with a last_seen strictly less than the
+                #      max last_seen. This hopefully results in deleting all but
+                #      one row the majority of the time, but there may be
+                #      duplicate last_seen
+                #   2. If multiple rows remain, we fall back to the naive method
+                #      and simply delete all rows and reinsert.
+                #
+                # Note that this relies on no new duplicate rows being inserted,
+                # but if that is happening then this entire process is futile
+                # anyway.
+
+                # Do step 1:
+
+                txn.execute(
+                    """
+                    DELETE FROM user_ips
+                    WHERE user_id = ? AND access_token = ? AND ip = ? AND last_seen < ?
+                    """,
+                    (user_id, access_token, ip, last_seen)
+                )
+                if txn.rowcount == count - 1:
+                    # We deleted all but one of the duplicate rows, i.e. there
+                    # is exactly one remaining and so there is nothing left to
+                    # do.
+                    continue
+                elif txn.rowcount >= count:
+                    raise Exception(
+                        "We deleted more duplicate rows from 'user_ips' than expected",
+                    )
+
+                # The previous step didn't delete enough rows, so we fallback to
+                # step 2:
 
                 # Drop all the duplicates
                 txn.execute(
diff --git a/synapse/storage/e2e_room_keys.py b/synapse/storage/e2e_room_keys.py
index 45cebe61d1..9a3aec759e 100644
--- a/synapse/storage/e2e_room_keys.py
+++ b/synapse/storage/e2e_room_keys.py
@@ -298,6 +298,27 @@ class EndToEndRoomKeyStore(SQLBaseStore):
             "create_e2e_room_keys_version_txn", _create_e2e_room_keys_version_txn
         )
 
+    def update_e2e_room_keys_version(self, user_id, version, info):
+        """Update a given backup version
+
+        Args:
+            user_id(str): the user whose backup version we're updating
+            version(str): the version ID of the backup version we're updating
+            info(dict): the new backup version info to store
+        """
+
+        return self._simple_update(
+            table="e2e_room_keys_versions",
+            keyvalues={
+                "user_id": user_id,
+                "version": version,
+            },
+            updatevalues={
+                "auth_data": json.dumps(info["auth_data"]),
+            },
+            desc="update_e2e_room_keys_version"
+        )
+
     def delete_e2e_room_keys_version(self, user_id, version=None):
         """Delete a given backup version of the user's room keys.
         Doesn't delete their actual key data.
diff --git a/synapse/storage/schema/delta/53/user_ips_index.sql b/synapse/storage/schema/delta/53/user_ips_index.sql
index 4ca346c111..b812c5794f 100644
--- a/synapse/storage/schema/delta/53/user_ips_index.sql
+++ b/synapse/storage/schema/delta/53/user_ips_index.sql
@@ -13,9 +13,13 @@
  * limitations under the License.
  */
 
--- delete duplicates
+ -- analyze user_ips, to help ensure the correct indices are used
 INSERT INTO background_updates (update_name, progress_json) VALUES
-  ('user_ips_remove_dupes', '{}');
+  ('user_ips_analyze', '{}');
+
+-- delete duplicates
+INSERT INTO background_updates (update_name, progress_json, depends_on) VALUES
+  ('user_ips_remove_dupes', '{}', 'user_ips_analyze');
 
 -- add a new unique index to user_ips table
 INSERT INTO background_updates (update_name, progress_json, depends_on) VALUES
@@ -23,4 +27,4 @@ INSERT INTO background_updates (update_name, progress_json, depends_on) VALUES
 
 -- drop the old original index
 INSERT INTO background_updates (update_name, progress_json, depends_on) VALUES
-  ('user_ips_drop_nonunique_index', '{}', 'user_ips_device_unique_index');
\ No newline at end of file
+  ('user_ips_drop_nonunique_index', '{}', 'user_ips_device_unique_index');