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-rw-r--r--synapse/app/homeserver.py2
-rw-r--r--synapse/config/logger.py4
-rw-r--r--synapse/federation/federation_client.py2
-rw-r--r--synapse/federation/sender/per_destination_queue.py8
-rw-r--r--synapse/handlers/device.py13
-rw-r--r--synapse/handlers/directory.py2
-rw-r--r--synapse/handlers/e2e_keys.py137
-rw-r--r--synapse/handlers/federation.py30
-rw-r--r--synapse/handlers/room.py8
-rw-r--r--synapse/handlers/room_member.py81
-rw-r--r--synapse/handlers/ui_auth/checkers.py2
-rw-r--r--synapse/http/client.py17
-rw-r--r--synapse/http/connectproxyclient.py195
-rw-r--r--synapse/http/proxyagent.py195
-rw-r--r--synapse/push/httppusher.py2
-rw-r--r--synapse/rest/client/v1/login.py2
-rw-r--r--synapse/rest/media/v1/preview_url_resource.py2
-rw-r--r--synapse/server.py9
-rw-r--r--synapse/server.pyi9
-rw-r--r--synapse/storage/data_stores/main/devices.py109
20 files changed, 752 insertions, 77 deletions
diff --git a/synapse/app/homeserver.py b/synapse/app/homeserver.py
index 8997c1f9e7..8d28076d92 100644
--- a/synapse/app/homeserver.py
+++ b/synapse/app/homeserver.py
@@ -565,7 +565,7 @@ def run(hs):
             "Reporting stats to %s: %s" % (hs.config.report_stats_endpoint, stats)
         )
         try:
-            yield hs.get_simple_http_client().put_json(
+            yield hs.get_proxied_http_client().put_json(
                 hs.config.report_stats_endpoint, stats
             )
         except Exception as e:
diff --git a/synapse/config/logger.py b/synapse/config/logger.py
index 2d2c1e54df..75bb904718 100644
--- a/synapse/config/logger.py
+++ b/synapse/config/logger.py
@@ -234,8 +234,8 @@ def setup_logging(
 
     # make sure that the first thing we log is a thing we can grep backwards
     # for
-    logging.warn("***** STARTING SERVER *****")
-    logging.warn("Server %s version %s", sys.argv[0], get_version_string(synapse))
+    logging.warning("***** STARTING SERVER *****")
+    logging.warning("Server %s version %s", sys.argv[0], get_version_string(synapse))
     logging.info("Server hostname: %s", config.server_name)
 
     return logger
diff --git a/synapse/federation/federation_client.py b/synapse/federation/federation_client.py
index 595706d01a..545d719652 100644
--- a/synapse/federation/federation_client.py
+++ b/synapse/federation/federation_client.py
@@ -555,7 +555,7 @@ class FederationClient(FederationBase):
         Note that this does not append any events to any graphs.
 
         Args:
-            destinations (str): Candidate homeservers which are probably
+            destinations (Iterable[str]): Candidate homeservers which are probably
                 participating in the room.
             room_id (str): The room in which the event will happen.
             user_id (str): The user whose membership is being evented.
diff --git a/synapse/federation/sender/per_destination_queue.py b/synapse/federation/sender/per_destination_queue.py
index b754a09d7a..a5b36b1827 100644
--- a/synapse/federation/sender/per_destination_queue.py
+++ b/synapse/federation/sender/per_destination_queue.py
@@ -360,20 +360,20 @@ class PerDestinationQueue(object):
         last_device_list = self._last_device_list_stream_id
 
         # Retrieve list of new device updates to send to the destination
-        now_stream_id, results = yield self._store.get_devices_by_remote(
+        now_stream_id, results = yield self._store.get_device_updates_by_remote(
             self._destination, last_device_list, limit=limit
         )
         edus = [
             Edu(
                 origin=self._server_name,
                 destination=self._destination,
-                edu_type="m.device_list_update",
+                edu_type=edu_type,
                 content=content,
             )
-            for content in results
+            for (edu_type, content) in results
         ]
 
-        assert len(edus) <= limit, "get_devices_by_remote returned too many EDUs"
+        assert len(edus) <= limit, "get_device_updates_by_remote returned too many EDUs"
 
         return (edus, now_stream_id)
 
diff --git a/synapse/handlers/device.py b/synapse/handlers/device.py
index 16b4617f68..26ef5e150c 100644
--- a/synapse/handlers/device.py
+++ b/synapse/handlers/device.py
@@ -459,7 +459,18 @@ class DeviceHandler(DeviceWorkerHandler):
     @defer.inlineCallbacks
     def on_federation_query_user_devices(self, user_id):
         stream_id, devices = yield self.store.get_devices_with_keys_by_user(user_id)
-        return {"user_id": user_id, "stream_id": stream_id, "devices": devices}
+        master_key = yield self.store.get_e2e_cross_signing_key(user_id, "master")
+        self_signing_key = yield self.store.get_e2e_cross_signing_key(
+            user_id, "self_signing"
+        )
+
+        return {
+            "user_id": user_id,
+            "stream_id": stream_id,
+            "devices": devices,
+            "master_key": master_key,
+            "self_signing_key": self_signing_key,
+        }
 
     @defer.inlineCallbacks
     def user_left_room(self, user, room_id):
diff --git a/synapse/handlers/directory.py b/synapse/handlers/directory.py
index 526379c6f7..c4632f8984 100644
--- a/synapse/handlers/directory.py
+++ b/synapse/handlers/directory.py
@@ -250,7 +250,7 @@ class DirectoryHandler(BaseHandler):
                     ignore_backoff=True,
                 )
             except CodeMessageException as e:
-                logging.warn("Error retrieving alias")
+                logging.warning("Error retrieving alias")
                 if e.code == 404:
                     result = None
                 else:
diff --git a/synapse/handlers/e2e_keys.py b/synapse/handlers/e2e_keys.py
index 0449034a4e..f09a0b73c8 100644
--- a/synapse/handlers/e2e_keys.py
+++ b/synapse/handlers/e2e_keys.py
@@ -36,6 +36,8 @@ from synapse.types import (
     get_verify_key_from_cross_signing_key,
 )
 from synapse.util import unwrapFirstError
+from synapse.util.async_helpers import Linearizer
+from synapse.util.caches.expiringcache import ExpiringCache
 from synapse.util.retryutils import NotRetryingDestination
 
 logger = logging.getLogger(__name__)
@@ -49,10 +51,19 @@ class E2eKeysHandler(object):
         self.is_mine = hs.is_mine
         self.clock = hs.get_clock()
 
+        self._edu_updater = SigningKeyEduUpdater(hs, self)
+
+        federation_registry = hs.get_federation_registry()
+
+        # FIXME: switch to m.signing_key_update when MSC1756 is merged into the spec
+        federation_registry.register_edu_handler(
+            "org.matrix.signing_key_update",
+            self._edu_updater.incoming_signing_key_update,
+        )
         # doesn't really work as part of the generic query API, because the
         # query request requires an object POST, but we abuse the
         # "query handler" interface.
-        hs.get_federation_registry().register_query_handler(
+        federation_registry.register_query_handler(
             "client_keys", self.on_federation_query_client_keys
         )
 
@@ -208,13 +219,15 @@ class E2eKeysHandler(object):
                     if user_id in destination_query:
                         results[user_id] = keys
 
-                for user_id, key in remote_result["master_keys"].items():
-                    if user_id in destination_query:
-                        cross_signing_keys["master_keys"][user_id] = key
+                if "master_keys" in remote_result:
+                    for user_id, key in remote_result["master_keys"].items():
+                        if user_id in destination_query:
+                            cross_signing_keys["master_keys"][user_id] = key
 
-                for user_id, key in remote_result["self_signing_keys"].items():
-                    if user_id in destination_query:
-                        cross_signing_keys["self_signing_keys"][user_id] = key
+                if "self_signing_keys" in remote_result:
+                    for user_id, key in remote_result["self_signing_keys"].items():
+                        if user_id in destination_query:
+                            cross_signing_keys["self_signing_keys"][user_id] = key
 
             except Exception as e:
                 failure = _exception_to_failure(e)
@@ -252,7 +265,7 @@ class E2eKeysHandler(object):
 
         Returns:
             defer.Deferred[dict[str, dict[str, dict]]]: map from
-                (master|self_signing|user_signing) -> user_id -> key
+                (master_keys|self_signing_keys|user_signing_keys) -> user_id -> key
         """
         master_keys = {}
         self_signing_keys = {}
@@ -344,7 +357,16 @@ class E2eKeysHandler(object):
         """
         device_keys_query = query_body.get("device_keys", {})
         res = yield self.query_local_devices(device_keys_query)
-        return {"device_keys": res}
+        ret = {"device_keys": res}
+
+        # add in the cross-signing keys
+        cross_signing_keys = yield self.get_cross_signing_keys_from_cache(
+            device_keys_query, None
+        )
+
+        ret.update(cross_signing_keys)
+
+        return ret
 
     @trace
     @defer.inlineCallbacks
@@ -1058,3 +1080,100 @@ class SignatureListItem:
     target_user_id = attr.ib()
     target_device_id = attr.ib()
     signature = attr.ib()
+
+
+class SigningKeyEduUpdater(object):
+    """Handles incoming signing key updates from federation and updates the DB"""
+
+    def __init__(self, hs, e2e_keys_handler):
+        self.store = hs.get_datastore()
+        self.federation = hs.get_federation_client()
+        self.clock = hs.get_clock()
+        self.e2e_keys_handler = e2e_keys_handler
+
+        self._remote_edu_linearizer = Linearizer(name="remote_signing_key")
+
+        # user_id -> list of updates waiting to be handled.
+        self._pending_updates = {}
+
+        # Recently seen stream ids. We don't bother keeping these in the DB,
+        # but they're useful to have them about to reduce the number of spurious
+        # resyncs.
+        self._seen_updates = ExpiringCache(
+            cache_name="signing_key_update_edu",
+            clock=self.clock,
+            max_len=10000,
+            expiry_ms=30 * 60 * 1000,
+            iterable=True,
+        )
+
+    @defer.inlineCallbacks
+    def incoming_signing_key_update(self, origin, edu_content):
+        """Called on incoming signing key update from federation. Responsible for
+        parsing the EDU and adding to pending updates list.
+
+        Args:
+            origin (string): the server that sent the EDU
+            edu_content (dict): the contents of the EDU
+        """
+
+        user_id = edu_content.pop("user_id")
+        master_key = edu_content.pop("master_key", None)
+        self_signing_key = edu_content.pop("self_signing_key", None)
+
+        if get_domain_from_id(user_id) != origin:
+            logger.warning("Got signing key update edu for %r from %r", user_id, origin)
+            return
+
+        room_ids = yield self.store.get_rooms_for_user(user_id)
+        if not room_ids:
+            # We don't share any rooms with this user. Ignore update, as we
+            # probably won't get any further updates.
+            return
+
+        self._pending_updates.setdefault(user_id, []).append(
+            (master_key, self_signing_key)
+        )
+
+        yield self._handle_signing_key_updates(user_id)
+
+    @defer.inlineCallbacks
+    def _handle_signing_key_updates(self, user_id):
+        """Actually handle pending updates.
+
+        Args:
+            user_id (string): the user whose updates we are processing
+        """
+
+        device_handler = self.e2e_keys_handler.device_handler
+
+        with (yield self._remote_edu_linearizer.queue(user_id)):
+            pending_updates = self._pending_updates.pop(user_id, [])
+            if not pending_updates:
+                # This can happen since we batch updates
+                return
+
+            device_ids = []
+
+            logger.info("pending updates: %r", pending_updates)
+
+            for master_key, self_signing_key in pending_updates:
+                if master_key:
+                    yield self.store.set_e2e_cross_signing_key(
+                        user_id, "master", master_key
+                    )
+                    _, verify_key = get_verify_key_from_cross_signing_key(master_key)
+                    # verify_key is a VerifyKey from signedjson, which uses
+                    # .version to denote the portion of the key ID after the
+                    # algorithm and colon, which is the device ID
+                    device_ids.append(verify_key.version)
+                if self_signing_key:
+                    yield self.store.set_e2e_cross_signing_key(
+                        user_id, "self_signing", self_signing_key
+                    )
+                    _, verify_key = get_verify_key_from_cross_signing_key(
+                        self_signing_key
+                    )
+                    device_ids.append(verify_key.version)
+
+            yield device_handler.notify_device_update(user_id, device_ids)
diff --git a/synapse/handlers/federation.py b/synapse/handlers/federation.py
index a932d3085f..dab6be9573 100644
--- a/synapse/handlers/federation.py
+++ b/synapse/handlers/federation.py
@@ -1106,7 +1106,7 @@ class FederationHandler(BaseHandler):
     @defer.inlineCallbacks
     def do_invite_join(self, target_hosts, room_id, joinee, content):
         """ Attempts to join the `joinee` to the room `room_id` via the
-        server `target_host`.
+        servers contained in `target_hosts`.
 
         This first triggers a /make_join/ request that returns a partial
         event that we can fill out and sign. This is then sent to the
@@ -1115,6 +1115,15 @@ class FederationHandler(BaseHandler):
 
         We suspend processing of any received events from this room until we
         have finished processing the join.
+
+        Args:
+            target_hosts (Iterable[str]): List of servers to attempt to join the room with.
+
+            room_id (str): The ID of the room to join.
+
+            joinee (str): The User ID of the joining user.
+
+            content (dict): The event content to use for the join event.
         """
         logger.debug("Joining %s to %s", joinee, room_id)
 
@@ -1174,6 +1183,22 @@ class FederationHandler(BaseHandler):
 
             yield self._persist_auth_tree(origin, auth_chain, state, event)
 
+            # Check whether this room is the result of an upgrade of a room we already know
+            # about. If so, migrate over user information
+            predecessor = yield self.store.get_room_predecessor(room_id)
+            if not predecessor:
+                return
+            old_room_id = predecessor["room_id"]
+            logger.debug(
+                "Found predecessor for %s during remote join: %s", room_id, old_room_id
+            )
+
+            # We retrieve the room member handler here as to not cause a cyclic dependency
+            member_handler = self.hs.get_room_member_handler()
+            yield member_handler.transfer_room_state_on_room_upgrade(
+                old_room_id, room_id
+            )
+
             logger.debug("Finished joining %s to %s", joinee, room_id)
         finally:
             room_queue = self.room_queues[room_id]
@@ -2442,6 +2467,8 @@ class FederationHandler(BaseHandler):
                 raise e
 
             yield self._check_signature(event, context)
+
+            # We retrieve the room member handler here as to not cause a cyclic dependency
             member_handler = self.hs.get_room_member_handler()
             yield member_handler.send_membership_event(None, event, context)
         else:
@@ -2502,6 +2529,7 @@ class FederationHandler(BaseHandler):
         # though the sender isn't a local user.
         event.internal_metadata.send_on_behalf_of = get_domain_from_id(event.sender)
 
+        # We retrieve the room member handler here as to not cause a cyclic dependency
         member_handler = self.hs.get_room_member_handler()
         yield member_handler.send_membership_event(None, event, context)
 
diff --git a/synapse/handlers/room.py b/synapse/handlers/room.py
index 0182e5b432..e92b2eafd5 100644
--- a/synapse/handlers/room.py
+++ b/synapse/handlers/room.py
@@ -129,6 +129,7 @@ class RoomCreationHandler(BaseHandler):
             old_room_id,
             new_version,  # args for _upgrade_room
         )
+
         return ret
 
     @defer.inlineCallbacks
@@ -189,7 +190,12 @@ class RoomCreationHandler(BaseHandler):
             requester, old_room_id, new_room_id, old_room_state
         )
 
-        # and finally, shut down the PLs in the old room, and update them in the new
+        # Copy over user push rules, tags and migrate room directory state
+        yield self.room_member_handler.transfer_room_state_on_room_upgrade(
+            old_room_id, new_room_id
+        )
+
+        # finally, shut down the PLs in the old room, and update them in the new
         # room.
         yield self._update_upgraded_room_pls(
             requester, old_room_id, new_room_id, old_room_state
diff --git a/synapse/handlers/room_member.py b/synapse/handlers/room_member.py
index 9a940d2c05..06d09c2947 100644
--- a/synapse/handlers/room_member.py
+++ b/synapse/handlers/room_member.py
@@ -203,10 +203,6 @@ class RoomMemberHandler(object):
                 prev_member_event = yield self.store.get_event(prev_member_event_id)
                 newly_joined = prev_member_event.membership != Membership.JOIN
             if newly_joined:
-                # Copy over user state if we're joining an upgraded room
-                yield self.copy_user_state_if_room_upgrade(
-                    room_id, requester.user.to_string()
-                )
                 yield self._user_joined_room(target, room_id)
         elif event.membership == Membership.LEAVE:
             if prev_member_event_id:
@@ -455,11 +451,6 @@ class RoomMemberHandler(object):
                     requester, remote_room_hosts, room_id, target, content
                 )
 
-                # Copy over user state if this is a join on an remote upgraded room
-                yield self.copy_user_state_if_room_upgrade(
-                    room_id, requester.user.to_string()
-                )
-
                 return remote_join_response
 
         elif effective_membership_state == Membership.LEAVE:
@@ -498,36 +489,72 @@ class RoomMemberHandler(object):
         return res
 
     @defer.inlineCallbacks
-    def copy_user_state_if_room_upgrade(self, new_room_id, user_id):
-        """Copy user-specific information when they join a new room if that new room is the
+    def transfer_room_state_on_room_upgrade(self, old_room_id, room_id):
+        """Upon our server becoming aware of an upgraded room, either by upgrading a room
+        ourselves or joining one, we can transfer over information from the previous room.
+
+        Copies user state (tags/push rules) for every local user that was in the old room, as
+        well as migrating the room directory state.
+
+        Args:
+            old_room_id (str): The ID of the old room
+
+            room_id (str): The ID of the new room
+
+        Returns:
+            Deferred
+        """
+        # Find all local users that were in the old room and copy over each user's state
+        users = yield self.store.get_users_in_room(old_room_id)
+        yield self.copy_user_state_on_room_upgrade(old_room_id, room_id, users)
+
+        # Add new room to the room directory if the old room was there
+        # Remove old room from the room directory
+        old_room = yield self.store.get_room(old_room_id)
+        if old_room and old_room["is_public"]:
+            yield self.store.set_room_is_public(old_room_id, False)
+            yield self.store.set_room_is_public(room_id, True)
+
+    @defer.inlineCallbacks
+    def copy_user_state_on_room_upgrade(self, old_room_id, new_room_id, user_ids):
+        """Copy user-specific information when they join a new room when that new room is the
         result of a room upgrade
 
         Args:
-            new_room_id (str): The ID of the room the user is joining
-            user_id (str): The ID of the user
+            old_room_id (str): The ID of upgraded room
+            new_room_id (str): The ID of the new room
+            user_ids (Iterable[str]): User IDs to copy state for
 
         Returns:
             Deferred
         """
-        # Check if the new room is an upgraded room
-        predecessor = yield self.store.get_room_predecessor(new_room_id)
-        if not predecessor:
-            return
 
         logger.debug(
-            "Found predecessor for %s: %s. Copying over room tags and push " "rules",
+            "Copying over room tags and push rules from %s to %s for users %s",
+            old_room_id,
             new_room_id,
-            predecessor,
+            user_ids,
         )
 
-        # It is an upgraded room. Copy over old tags
-        yield self.copy_room_tags_and_direct_to_room(
-            predecessor["room_id"], new_room_id, user_id
-        )
-        # Copy over push rules
-        yield self.store.copy_push_rules_from_room_to_room_for_user(
-            predecessor["room_id"], new_room_id, user_id
-        )
+        for user_id in user_ids:
+            try:
+                # It is an upgraded room. Copy over old tags
+                yield self.copy_room_tags_and_direct_to_room(
+                    old_room_id, new_room_id, user_id
+                )
+                # Copy over push rules
+                yield self.store.copy_push_rules_from_room_to_room_for_user(
+                    old_room_id, new_room_id, user_id
+                )
+            except Exception:
+                logger.exception(
+                    "Error copying tags and/or push rules from rooms %s to %s for user %s. "
+                    "Skipping...",
+                    old_room_id,
+                    new_room_id,
+                    user_id,
+                )
+                continue
 
     @defer.inlineCallbacks
     def send_membership_event(self, requester, event, context, ratelimit=True):
diff --git a/synapse/handlers/ui_auth/checkers.py b/synapse/handlers/ui_auth/checkers.py
index 29aa1e5aaf..8363d887a9 100644
--- a/synapse/handlers/ui_auth/checkers.py
+++ b/synapse/handlers/ui_auth/checkers.py
@@ -81,7 +81,7 @@ class RecaptchaAuthChecker(UserInteractiveAuthChecker):
     def __init__(self, hs):
         super().__init__(hs)
         self._enabled = bool(hs.config.recaptcha_private_key)
-        self._http_client = hs.get_simple_http_client()
+        self._http_client = hs.get_proxied_http_client()
         self._url = hs.config.recaptcha_siteverify_api
         self._secret = hs.config.recaptcha_private_key
 
diff --git a/synapse/http/client.py b/synapse/http/client.py
index 2df5b383b5..d4c285445e 100644
--- a/synapse/http/client.py
+++ b/synapse/http/client.py
@@ -45,6 +45,7 @@ from synapse.http import (
     cancelled_to_request_timed_out_error,
     redact_uri,
 )
+from synapse.http.proxyagent import ProxyAgent
 from synapse.logging.context import make_deferred_yieldable
 from synapse.logging.opentracing import set_tag, start_active_span, tags
 from synapse.util.async_helpers import timeout_deferred
@@ -183,7 +184,15 @@ class SimpleHttpClient(object):
     using HTTP in Matrix
     """
 
-    def __init__(self, hs, treq_args={}, ip_whitelist=None, ip_blacklist=None):
+    def __init__(
+        self,
+        hs,
+        treq_args={},
+        ip_whitelist=None,
+        ip_blacklist=None,
+        http_proxy=None,
+        https_proxy=None,
+    ):
         """
         Args:
             hs (synapse.server.HomeServer)
@@ -192,6 +201,8 @@ class SimpleHttpClient(object):
                 we may not request.
             ip_whitelist (netaddr.IPSet): The whitelisted IP addresses, that we can
                request if it were otherwise caught in a blacklist.
+            http_proxy (bytes): proxy server to use for http connections. host[:port]
+            https_proxy (bytes): proxy server to use for https connections. host[:port]
         """
         self.hs = hs
 
@@ -236,11 +247,13 @@ class SimpleHttpClient(object):
         # The default context factory in Twisted 14.0.0 (which we require) is
         # BrowserLikePolicyForHTTPS which will do regular cert validation
         # 'like a browser'
-        self.agent = Agent(
+        self.agent = ProxyAgent(
             self.reactor,
             connectTimeout=15,
             contextFactory=self.hs.get_http_client_context_factory(),
             pool=pool,
+            http_proxy=http_proxy,
+            https_proxy=https_proxy,
         )
 
         if self._ip_blacklist:
diff --git a/synapse/http/connectproxyclient.py b/synapse/http/connectproxyclient.py
new file mode 100644
index 0000000000..be7b2ceb8e
--- /dev/null
+++ b/synapse/http/connectproxyclient.py
@@ -0,0 +1,195 @@
+# -*- coding: utf-8 -*-
+# Copyright 2019 The Matrix.org Foundation C.I.C.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+import logging
+
+from zope.interface import implementer
+
+from twisted.internet import defer, protocol
+from twisted.internet.error import ConnectError
+from twisted.internet.interfaces import IStreamClientEndpoint
+from twisted.internet.protocol import connectionDone
+from twisted.web import http
+
+logger = logging.getLogger(__name__)
+
+
+class ProxyConnectError(ConnectError):
+    pass
+
+
+@implementer(IStreamClientEndpoint)
+class HTTPConnectProxyEndpoint(object):
+    """An Endpoint implementation which will send a CONNECT request to an http proxy
+
+    Wraps an existing HostnameEndpoint for the proxy.
+
+    When we get the connect() request from the connection pool (via the TLS wrapper),
+    we'll first connect to the proxy endpoint with a ProtocolFactory which will make the
+    CONNECT request. Once that completes, we invoke the protocolFactory which was passed
+    in.
+
+    Args:
+        reactor: the Twisted reactor to use for the connection
+        proxy_endpoint (IStreamClientEndpoint): the endpoint to use to connect to the
+            proxy
+        host (bytes): hostname that we want to CONNECT to
+        port (int): port that we want to connect to
+    """
+
+    def __init__(self, reactor, proxy_endpoint, host, port):
+        self._reactor = reactor
+        self._proxy_endpoint = proxy_endpoint
+        self._host = host
+        self._port = port
+
+    def __repr__(self):
+        return "<HTTPConnectProxyEndpoint %s>" % (self._proxy_endpoint,)
+
+    def connect(self, protocolFactory):
+        f = HTTPProxiedClientFactory(self._host, self._port, protocolFactory)
+        d = self._proxy_endpoint.connect(f)
+        # once the tcp socket connects successfully, we need to wait for the
+        # CONNECT to complete.
+        d.addCallback(lambda conn: f.on_connection)
+        return d
+
+
+class HTTPProxiedClientFactory(protocol.ClientFactory):
+    """ClientFactory wrapper that triggers an HTTP proxy CONNECT on connect.
+
+    Once the CONNECT completes, invokes the original ClientFactory to build the
+    HTTP Protocol object and run the rest of the connection.
+
+    Args:
+        dst_host (bytes): hostname that we want to CONNECT to
+        dst_port (int): port that we want to connect to
+        wrapped_factory (protocol.ClientFactory): The original Factory
+    """
+
+    def __init__(self, dst_host, dst_port, wrapped_factory):
+        self.dst_host = dst_host
+        self.dst_port = dst_port
+        self.wrapped_factory = wrapped_factory
+        self.on_connection = defer.Deferred()
+
+    def startedConnecting(self, connector):
+        return self.wrapped_factory.startedConnecting(connector)
+
+    def buildProtocol(self, addr):
+        wrapped_protocol = self.wrapped_factory.buildProtocol(addr)
+
+        return HTTPConnectProtocol(
+            self.dst_host, self.dst_port, wrapped_protocol, self.on_connection
+        )
+
+    def clientConnectionFailed(self, connector, reason):
+        logger.debug("Connection to proxy failed: %s", reason)
+        if not self.on_connection.called:
+            self.on_connection.errback(reason)
+        return self.wrapped_factory.clientConnectionFailed(connector, reason)
+
+    def clientConnectionLost(self, connector, reason):
+        logger.debug("Connection to proxy lost: %s", reason)
+        if not self.on_connection.called:
+            self.on_connection.errback(reason)
+        return self.wrapped_factory.clientConnectionLost(connector, reason)
+
+
+class HTTPConnectProtocol(protocol.Protocol):
+    """Protocol that wraps an existing Protocol to do a CONNECT handshake at connect
+
+    Args:
+        host (bytes): The original HTTP(s) hostname or IPv4 or IPv6 address literal
+            to put in the CONNECT request
+
+        port (int): The original HTTP(s) port to put in the CONNECT request
+
+        wrapped_protocol (interfaces.IProtocol): the original protocol (probably
+            HTTPChannel or TLSMemoryBIOProtocol, but could be anything really)
+
+        connected_deferred (Deferred): a Deferred which will be callbacked with
+            wrapped_protocol when the CONNECT completes
+    """
+
+    def __init__(self, host, port, wrapped_protocol, connected_deferred):
+        self.host = host
+        self.port = port
+        self.wrapped_protocol = wrapped_protocol
+        self.connected_deferred = connected_deferred
+        self.http_setup_client = HTTPConnectSetupClient(self.host, self.port)
+        self.http_setup_client.on_connected.addCallback(self.proxyConnected)
+
+    def connectionMade(self):
+        self.http_setup_client.makeConnection(self.transport)
+
+    def connectionLost(self, reason=connectionDone):
+        if self.wrapped_protocol.connected:
+            self.wrapped_protocol.connectionLost(reason)
+
+        self.http_setup_client.connectionLost(reason)
+
+        if not self.connected_deferred.called:
+            self.connected_deferred.errback(reason)
+
+    def proxyConnected(self, _):
+        self.wrapped_protocol.makeConnection(self.transport)
+
+        self.connected_deferred.callback(self.wrapped_protocol)
+
+        # Get any pending data from the http buf and forward it to the original protocol
+        buf = self.http_setup_client.clearLineBuffer()
+        if buf:
+            self.wrapped_protocol.dataReceived(buf)
+
+    def dataReceived(self, data):
+        # if we've set up the HTTP protocol, we can send the data there
+        if self.wrapped_protocol.connected:
+            return self.wrapped_protocol.dataReceived(data)
+
+        # otherwise, we must still be setting up the connection: send the data to the
+        # setup client
+        return self.http_setup_client.dataReceived(data)
+
+
+class HTTPConnectSetupClient(http.HTTPClient):
+    """HTTPClient protocol to send a CONNECT message for proxies and read the response.
+
+    Args:
+        host (bytes): The hostname to send in the CONNECT message
+        port (int): The port to send in the CONNECT message
+    """
+
+    def __init__(self, host, port):
+        self.host = host
+        self.port = port
+        self.on_connected = defer.Deferred()
+
+    def connectionMade(self):
+        logger.debug("Connected to proxy, sending CONNECT")
+        self.sendCommand(b"CONNECT", b"%s:%d" % (self.host, self.port))
+        self.endHeaders()
+
+    def handleStatus(self, version, status, message):
+        logger.debug("Got Status: %s %s %s", status, message, version)
+        if status != b"200":
+            raise ProxyConnectError("Unexpected status on CONNECT: %s" % status)
+
+    def handleEndHeaders(self):
+        logger.debug("End Headers")
+        self.on_connected.callback(None)
+
+    def handleResponse(self, body):
+        pass
diff --git a/synapse/http/proxyagent.py b/synapse/http/proxyagent.py
new file mode 100644
index 0000000000..332da02a8d
--- /dev/null
+++ b/synapse/http/proxyagent.py
@@ -0,0 +1,195 @@
+# -*- coding: utf-8 -*-
+# Copyright 2019 The Matrix.org Foundation C.I.C.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+import logging
+import re
+
+from zope.interface import implementer
+
+from twisted.internet import defer
+from twisted.internet.endpoints import HostnameEndpoint, wrapClientTLS
+from twisted.python.failure import Failure
+from twisted.web.client import URI, BrowserLikePolicyForHTTPS, _AgentBase
+from twisted.web.error import SchemeNotSupported
+from twisted.web.iweb import IAgent
+
+from synapse.http.connectproxyclient import HTTPConnectProxyEndpoint
+
+logger = logging.getLogger(__name__)
+
+_VALID_URI = re.compile(br"\A[\x21-\x7e]+\Z")
+
+
+@implementer(IAgent)
+class ProxyAgent(_AgentBase):
+    """An Agent implementation which will use an HTTP proxy if one was requested
+
+    Args:
+        reactor: twisted reactor to place outgoing
+            connections.
+
+        contextFactory (IPolicyForHTTPS): A factory for TLS contexts, to control the
+            verification parameters of OpenSSL.  The default is to use a
+            `BrowserLikePolicyForHTTPS`, so unless you have special
+            requirements you can leave this as-is.
+
+        connectTimeout (float): The amount of time that this Agent will wait
+            for the peer to accept a connection.
+
+        bindAddress (bytes): The local address for client sockets to bind to.
+
+        pool (HTTPConnectionPool|None): connection pool to be used. If None, a
+            non-persistent pool instance will be created.
+    """
+
+    def __init__(
+        self,
+        reactor,
+        contextFactory=BrowserLikePolicyForHTTPS(),
+        connectTimeout=None,
+        bindAddress=None,
+        pool=None,
+        http_proxy=None,
+        https_proxy=None,
+    ):
+        _AgentBase.__init__(self, reactor, pool)
+
+        self._endpoint_kwargs = {}
+        if connectTimeout is not None:
+            self._endpoint_kwargs["timeout"] = connectTimeout
+        if bindAddress is not None:
+            self._endpoint_kwargs["bindAddress"] = bindAddress
+
+        self.http_proxy_endpoint = _http_proxy_endpoint(
+            http_proxy, reactor, **self._endpoint_kwargs
+        )
+
+        self.https_proxy_endpoint = _http_proxy_endpoint(
+            https_proxy, reactor, **self._endpoint_kwargs
+        )
+
+        self._policy_for_https = contextFactory
+        self._reactor = reactor
+
+    def request(self, method, uri, headers=None, bodyProducer=None):
+        """
+        Issue a request to the server indicated by the given uri.
+
+        Supports `http` and `https` schemes.
+
+        An existing connection from the connection pool may be used or a new one may be
+        created.
+
+        See also: twisted.web.iweb.IAgent.request
+
+        Args:
+            method (bytes): The request method to use, such as `GET`, `POST`, etc
+
+            uri (bytes): The location of the resource to request.
+
+            headers (Headers|None): Extra headers to send with the request
+
+            bodyProducer (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[IResponse]: completes when the header of the response has
+                 been received (regardless of the response status code).
+        """
+        uri = uri.strip()
+        if not _VALID_URI.match(uri):
+            raise ValueError("Invalid URI {!r}".format(uri))
+
+        parsed_uri = URI.fromBytes(uri)
+        pool_key = (parsed_uri.scheme, parsed_uri.host, parsed_uri.port)
+        request_path = parsed_uri.originForm
+
+        if parsed_uri.scheme == b"http" and self.http_proxy_endpoint:
+            # Cache *all* connections under the same key, since we are only
+            # connecting to a single destination, the proxy:
+            pool_key = ("http-proxy", self.http_proxy_endpoint)
+            endpoint = self.http_proxy_endpoint
+            request_path = uri
+        elif parsed_uri.scheme == b"https" and self.https_proxy_endpoint:
+            endpoint = HTTPConnectProxyEndpoint(
+                self._reactor,
+                self.https_proxy_endpoint,
+                parsed_uri.host,
+                parsed_uri.port,
+            )
+        else:
+            # not using a proxy
+            endpoint = HostnameEndpoint(
+                self._reactor, parsed_uri.host, parsed_uri.port, **self._endpoint_kwargs
+            )
+
+        logger.debug("Requesting %s via %s", uri, endpoint)
+
+        if parsed_uri.scheme == b"https":
+            tls_connection_creator = self._policy_for_https.creatorForNetloc(
+                parsed_uri.host, parsed_uri.port
+            )
+            endpoint = wrapClientTLS(tls_connection_creator, endpoint)
+        elif parsed_uri.scheme == b"http":
+            pass
+        else:
+            return defer.fail(
+                Failure(
+                    SchemeNotSupported("Unsupported scheme: %r" % (parsed_uri.scheme,))
+                )
+            )
+
+        return self._requestWithEndpoint(
+            pool_key, endpoint, method, parsed_uri, headers, bodyProducer, request_path
+        )
+
+
+def _http_proxy_endpoint(proxy, reactor, **kwargs):
+    """Parses an http proxy setting and returns an endpoint for the proxy
+
+    Args:
+        proxy (bytes|None):  the proxy setting
+        reactor: reactor to be used to connect to the proxy
+        kwargs: other args to be passed to HostnameEndpoint
+
+    Returns:
+        interfaces.IStreamClientEndpoint|None: endpoint to use to connect to the proxy,
+            or None
+    """
+    if proxy is None:
+        return None
+
+    # currently we only support hostname:port. Some apps also support
+    # protocol://<host>[:port], which allows a way of requiring a TLS connection to the
+    # proxy.
+
+    host, port = parse_host_port(proxy, default_port=1080)
+    return HostnameEndpoint(reactor, host, port, **kwargs)
+
+
+def parse_host_port(hostport, default_port=None):
+    # could have sworn we had one of these somewhere else...
+    if b":" in hostport:
+        host, port = hostport.rsplit(b":", 1)
+        try:
+            port = int(port)
+            return host, port
+        except ValueError:
+            # the thing after the : wasn't a valid port; presumably this is an
+            # IPv6 address.
+            pass
+
+    return hostport, default_port
diff --git a/synapse/push/httppusher.py b/synapse/push/httppusher.py
index 7dde2ad055..e994037be6 100644
--- a/synapse/push/httppusher.py
+++ b/synapse/push/httppusher.py
@@ -103,7 +103,7 @@ class HttpPusher(object):
         if "url" not in self.data:
             raise PusherConfigException("'url' required in data for HTTP pusher")
         self.url = self.data["url"]
-        self.http_client = hs.get_simple_http_client()
+        self.http_client = hs.get_proxied_http_client()
         self.data_minus_url = {}
         self.data_minus_url.update(self.data)
         del self.data_minus_url["url"]
diff --git a/synapse/rest/client/v1/login.py b/synapse/rest/client/v1/login.py
index 00a7dd6d09..24a0ce74f2 100644
--- a/synapse/rest/client/v1/login.py
+++ b/synapse/rest/client/v1/login.py
@@ -381,7 +381,7 @@ class CasTicketServlet(RestServlet):
         self.cas_displayname_attribute = hs.config.cas_displayname_attribute
         self.cas_required_attributes = hs.config.cas_required_attributes
         self._sso_auth_handler = SSOAuthHandler(hs)
-        self._http_client = hs.get_simple_http_client()
+        self._http_client = hs.get_proxied_http_client()
 
     @defer.inlineCallbacks
     def on_GET(self, request):
diff --git a/synapse/rest/media/v1/preview_url_resource.py b/synapse/rest/media/v1/preview_url_resource.py
index 5a25b6b3fc..531d923f76 100644
--- a/synapse/rest/media/v1/preview_url_resource.py
+++ b/synapse/rest/media/v1/preview_url_resource.py
@@ -74,6 +74,8 @@ class PreviewUrlResource(DirectServeResource):
             treq_args={"browser_like_redirects": True},
             ip_whitelist=hs.config.url_preview_ip_range_whitelist,
             ip_blacklist=hs.config.url_preview_ip_range_blacklist,
+            http_proxy=os.getenv("http_proxy"),
+            https_proxy=os.getenv("HTTPS_PROXY"),
         )
         self.media_repo = media_repo
         self.primary_base_path = media_repo.primary_base_path
diff --git a/synapse/server.py b/synapse/server.py
index 0b81af646c..f8aeebcff8 100644
--- a/synapse/server.py
+++ b/synapse/server.py
@@ -23,6 +23,7 @@
 # Imports required for the default HomeServer() implementation
 import abc
 import logging
+import os
 
 from twisted.enterprise import adbapi
 from twisted.mail.smtp import sendmail
@@ -168,6 +169,7 @@ class HomeServer(object):
         "filtering",
         "http_client_context_factory",
         "simple_http_client",
+        "proxied_http_client",
         "media_repository",
         "media_repository_resource",
         "federation_transport_client",
@@ -311,6 +313,13 @@ class HomeServer(object):
     def build_simple_http_client(self):
         return SimpleHttpClient(self)
 
+    def build_proxied_http_client(self):
+        return SimpleHttpClient(
+            self,
+            http_proxy=os.getenv("http_proxy"),
+            https_proxy=os.getenv("HTTPS_PROXY"),
+        )
+
     def build_room_creation_handler(self):
         return RoomCreationHandler(self)
 
diff --git a/synapse/server.pyi b/synapse/server.pyi
index 83d1f11283..b5e0b57095 100644
--- a/synapse/server.pyi
+++ b/synapse/server.pyi
@@ -12,6 +12,7 @@ import synapse.handlers.message
 import synapse.handlers.room
 import synapse.handlers.room_member
 import synapse.handlers.set_password
+import synapse.http.client
 import synapse.rest.media.v1.media_repository
 import synapse.server_notices.server_notices_manager
 import synapse.server_notices.server_notices_sender
@@ -38,6 +39,14 @@ class HomeServer(object):
         pass
     def get_state_resolution_handler(self) -> synapse.state.StateResolutionHandler:
         pass
+    def get_simple_http_client(self) -> synapse.http.client.SimpleHttpClient:
+        """Fetch an HTTP client implementation which doesn't do any blacklisting
+        or support any HTTP_PROXY settings"""
+        pass
+    def get_proxied_http_client(self) -> synapse.http.client.SimpleHttpClient:
+        """Fetch an HTTP client implementation which doesn't do any blacklisting
+        but does support HTTP_PROXY settings"""
+        pass
     def get_deactivate_account_handler(
         self,
     ) -> synapse.handlers.deactivate_account.DeactivateAccountHandler:
diff --git a/synapse/storage/data_stores/main/devices.py b/synapse/storage/data_stores/main/devices.py
index f7a3542348..71f62036c0 100644
--- a/synapse/storage/data_stores/main/devices.py
+++ b/synapse/storage/data_stores/main/devices.py
@@ -37,6 +37,7 @@ from synapse.storage._base import (
     make_in_list_sql_clause,
 )
 from synapse.storage.background_updates import BackgroundUpdateStore
+from synapse.types import get_verify_key_from_cross_signing_key
 from synapse.util import batch_iter
 from synapse.util.caches.descriptors import cached, cachedInlineCallbacks, cachedList
 
@@ -90,13 +91,18 @@ class DeviceWorkerStore(SQLBaseStore):
 
     @trace
     @defer.inlineCallbacks
-    def get_devices_by_remote(self, destination, from_stream_id, limit):
-        """Get stream of updates to send to remote servers
+    def get_device_updates_by_remote(self, destination, from_stream_id, limit):
+        """Get a stream of device updates to send to the given remote server.
 
+        Args:
+            destination (str): The host the device updates are intended for
+            from_stream_id (int): The minimum stream_id to filter updates by, exclusive
+            limit (int): Maximum number of device updates to return
         Returns:
-            Deferred[tuple[int, list[dict]]]:
+            Deferred[tuple[int, list[tuple[string,dict]]]]:
                 current stream id (ie, the stream id of the last update included in the
-                response), and the list of updates
+                response), and the list of updates, where each update is a pair of EDU
+                type and EDU contents
         """
         now_stream_id = self._device_list_id_gen.get_current_token()
 
@@ -117,8 +123,8 @@ class DeviceWorkerStore(SQLBaseStore):
         # stream_id; the rationale being that such a large device list update
         # is likely an error.
         updates = yield self.runInteraction(
-            "get_devices_by_remote",
-            self._get_devices_by_remote_txn,
+            "get_device_updates_by_remote",
+            self._get_device_updates_by_remote_txn,
             destination,
             from_stream_id,
             now_stream_id,
@@ -129,6 +135,37 @@ class DeviceWorkerStore(SQLBaseStore):
         if not updates:
             return now_stream_id, []
 
+        # get the cross-signing keys of the users in the list, so that we can
+        # determine which of the device changes were cross-signing keys
+        users = set(r[0] for r in updates)
+        master_key_by_user = {}
+        self_signing_key_by_user = {}
+        for user in users:
+            cross_signing_key = yield self.get_e2e_cross_signing_key(user, "master")
+            if cross_signing_key:
+                key_id, verify_key = get_verify_key_from_cross_signing_key(
+                    cross_signing_key
+                )
+                # verify_key is a VerifyKey from signedjson, which uses
+                # .version to denote the portion of the key ID after the
+                # algorithm and colon, which is the device ID
+                master_key_by_user[user] = {
+                    "key_info": cross_signing_key,
+                    "device_id": verify_key.version,
+                }
+
+            cross_signing_key = yield self.get_e2e_cross_signing_key(
+                user, "self_signing"
+            )
+            if cross_signing_key:
+                key_id, verify_key = get_verify_key_from_cross_signing_key(
+                    cross_signing_key
+                )
+                self_signing_key_by_user[user] = {
+                    "key_info": cross_signing_key,
+                    "device_id": verify_key.version,
+                }
+
         # if we have exceeded the limit, we need to exclude any results with the
         # same stream_id as the last row.
         if len(updates) > limit:
@@ -153,20 +190,33 @@ class DeviceWorkerStore(SQLBaseStore):
         # context which created the Edu.
 
         query_map = {}
-        for update in updates:
-            if stream_id_cutoff is not None and update[2] >= stream_id_cutoff:
+        cross_signing_keys_by_user = {}
+        for user_id, device_id, update_stream_id, update_context in updates:
+            if stream_id_cutoff is not None and update_stream_id >= stream_id_cutoff:
                 # Stop processing updates
                 break
 
-            key = (update[0], update[1])
-
-            update_context = update[3]
-            update_stream_id = update[2]
+            if (
+                user_id in master_key_by_user
+                and device_id == master_key_by_user[user_id]["device_id"]
+            ):
+                result = cross_signing_keys_by_user.setdefault(user_id, {})
+                result["master_key"] = master_key_by_user[user_id]["key_info"]
+            elif (
+                user_id in self_signing_key_by_user
+                and device_id == self_signing_key_by_user[user_id]["device_id"]
+            ):
+                result = cross_signing_keys_by_user.setdefault(user_id, {})
+                result["self_signing_key"] = self_signing_key_by_user[user_id][
+                    "key_info"
+                ]
+            else:
+                key = (user_id, device_id)
 
-            previous_update_stream_id, _ = query_map.get(key, (0, None))
+                previous_update_stream_id, _ = query_map.get(key, (0, None))
 
-            if update_stream_id > previous_update_stream_id:
-                query_map[key] = (update_stream_id, update_context)
+                if update_stream_id > previous_update_stream_id:
+                    query_map[key] = (update_stream_id, update_context)
 
         # If we didn't find any updates with a stream_id lower than the cutoff, it
         # means that there are more than limit updates all of which have the same
@@ -176,16 +226,22 @@ class DeviceWorkerStore(SQLBaseStore):
         # devices, in which case E2E isn't going to work well anyway. We'll just
         # skip that stream_id and return an empty list, and continue with the next
         # stream_id next time.
-        if not query_map:
+        if not query_map and not cross_signing_keys_by_user:
             return stream_id_cutoff, []
 
         results = yield self._get_device_update_edus_by_remote(
             destination, from_stream_id, query_map
         )
 
+        # add the updated cross-signing keys to the results list
+        for user_id, result in iteritems(cross_signing_keys_by_user):
+            result["user_id"] = user_id
+            # FIXME: switch to m.signing_key_update when MSC1756 is merged into the spec
+            results.append(("org.matrix.signing_key_update", result))
+
         return now_stream_id, results
 
-    def _get_devices_by_remote_txn(
+    def _get_device_updates_by_remote_txn(
         self, txn, destination, from_stream_id, now_stream_id, limit
     ):
         """Return device update information for a given remote destination
@@ -200,6 +256,7 @@ class DeviceWorkerStore(SQLBaseStore):
         Returns:
             List: List of device updates
         """
+        # get the list of device updates that need to be sent
         sql = """
             SELECT user_id, device_id, stream_id, opentracing_context FROM device_lists_outbound_pokes
             WHERE destination = ? AND ? < stream_id AND stream_id <= ? AND sent = ?
@@ -225,12 +282,16 @@ class DeviceWorkerStore(SQLBaseStore):
             List[Dict]: List of objects representing an device update EDU
 
         """
-        devices = yield self.runInteraction(
-            "_get_e2e_device_keys_txn",
-            self._get_e2e_device_keys_txn,
-            query_map.keys(),
-            include_all_devices=True,
-            include_deleted_devices=True,
+        devices = (
+            yield self.runInteraction(
+                "_get_e2e_device_keys_txn",
+                self._get_e2e_device_keys_txn,
+                query_map.keys(),
+                include_all_devices=True,
+                include_deleted_devices=True,
+            )
+            if query_map
+            else {}
         )
 
         results = []
@@ -262,7 +323,7 @@ class DeviceWorkerStore(SQLBaseStore):
                 else:
                     result["deleted"] = True
 
-                results.append(result)
+                results.append(("m.device_list_update", result))
 
         return results