Merge branch 'release-v0.24.0' of github.com:matrix-org/synapse v0.24.0

11 files changed, 1251 insertions, 228 deletions

diff --git a/synapse/rest/__init__.py b/synapse/rest/__init__.py
index 3d809d181b..16f5a73b95 100644
--- a/synapse/rest/__init__.py
+++ b/synapse/rest/__init__.py
@@ -52,6 +52,7 @@ from synapse.rest.client.v2_alpha import (
     thirdparty,
     sendtodevice,
     user_directory,
+    groups,
 )
 
 from synapse.http.server import JsonResource
@@ -102,3 +103,4 @@ class ClientRestResource(JsonResource):
         thirdparty.register_servlets(hs, client_resource)
         sendtodevice.register_servlets(hs, client_resource)
         user_directory.register_servlets(hs, client_resource)
+        groups.register_servlets(hs, client_resource)
diff --git a/synapse/rest/client/v1/profile.py b/synapse/rest/client/v1/profile.py
index 1a5045c9ec..d7edc34245 100644
--- a/synapse/rest/client/v1/profile.py
+++ b/synapse/rest/client/v1/profile.py
@@ -26,13 +26,13 @@ class ProfileDisplaynameRestServlet(ClientV1RestServlet):
 
     def __init__(self, hs):
         super(ProfileDisplaynameRestServlet, self).__init__(hs)
-        self.handlers = hs.get_handlers()
+        self.profile_handler = hs.get_profile_handler()
 
     @defer.inlineCallbacks
     def on_GET(self, request, user_id):
         user = UserID.from_string(user_id)
 
-        displayname = yield self.handlers.profile_handler.get_displayname(
+        displayname = yield self.profile_handler.get_displayname(
             user,
         )
 
@@ -55,7 +55,7 @@ class ProfileDisplaynameRestServlet(ClientV1RestServlet):
         except:
             defer.returnValue((400, "Unable to parse name"))
 
-        yield self.handlers.profile_handler.set_displayname(
+        yield self.profile_handler.set_displayname(
             user, requester, new_name, is_admin)
 
         defer.returnValue((200, {}))
@@ -69,13 +69,13 @@ class ProfileAvatarURLRestServlet(ClientV1RestServlet):
 
     def __init__(self, hs):
         super(ProfileAvatarURLRestServlet, self).__init__(hs)
-        self.handlers = hs.get_handlers()
+        self.profile_handler = hs.get_profile_handler()
 
     @defer.inlineCallbacks
     def on_GET(self, request, user_id):
         user = UserID.from_string(user_id)
 
-        avatar_url = yield self.handlers.profile_handler.get_avatar_url(
+        avatar_url = yield self.profile_handler.get_avatar_url(
             user,
         )
 
@@ -97,7 +97,7 @@ class ProfileAvatarURLRestServlet(ClientV1RestServlet):
         except:
             defer.returnValue((400, "Unable to parse name"))
 
-        yield self.handlers.profile_handler.set_avatar_url(
+        yield self.profile_handler.set_avatar_url(
             user, requester, new_name, is_admin)
 
         defer.returnValue((200, {}))
@@ -111,16 +111,16 @@ class ProfileRestServlet(ClientV1RestServlet):
 
     def __init__(self, hs):
         super(ProfileRestServlet, self).__init__(hs)
-        self.handlers = hs.get_handlers()
+        self.profile_handler = hs.get_profile_handler()
 
     @defer.inlineCallbacks
     def on_GET(self, request, user_id):
         user = UserID.from_string(user_id)
 
-        displayname = yield self.handlers.profile_handler.get_displayname(
+        displayname = yield self.profile_handler.get_displayname(
             user,
         )
-        avatar_url = yield self.handlers.profile_handler.get_avatar_url(
+        avatar_url = yield self.profile_handler.get_avatar_url(
             user,
         )
 
diff --git a/synapse/rest/client/v1/room.py b/synapse/rest/client/v1/room.py
index cd388770c8..6c379d53ac 100644
--- a/synapse/rest/client/v1/room.py
+++ b/synapse/rest/client/v1/room.py
@@ -398,22 +398,18 @@ class JoinedRoomMemberListRestServlet(ClientV1RestServlet):
 
     def __init__(self, hs):
         super(JoinedRoomMemberListRestServlet, self).__init__(hs)
-        self.state = hs.get_state_handler()
+        self.message_handler = hs.get_handlers().message_handler
 
     @defer.inlineCallbacks
     def on_GET(self, request, room_id):
-        yield self.auth.get_user_by_req(request)
+        requester = yield self.auth.get_user_by_req(request)
 
-        users_with_profile = yield self.state.get_current_user_in_room(room_id)
+        users_with_profile = yield self.message_handler.get_joined_members(
+            requester, room_id,
+        )
 
         defer.returnValue((200, {
-            "joined": {
-                user_id: {
-                    "avatar_url": profile.avatar_url,
-                    "display_name": profile.display_name,
-                }
-                for user_id, profile in users_with_profile.iteritems()
-            }
+            "joined": users_with_profile,
         }))
 
 
diff --git a/synapse/rest/client/v2_alpha/groups.py b/synapse/rest/client/v2_alpha/groups.py
new file mode 100644
index 0000000000..d11bccc1da
--- /dev/null
+++ b/synapse/rest/client/v2_alpha/groups.py
@@ -0,0 +1,717 @@
+# -*- coding: utf-8 -*-
+# Copyright 2017 Vector Creations Ltd
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+from twisted.internet import defer
+
+from synapse.http.servlet import RestServlet, parse_json_object_from_request
+from synapse.types import GroupID
+
+from ._base import client_v2_patterns
+
+import logging
+
+logger = logging.getLogger(__name__)
+
+
+class GroupServlet(RestServlet):
+    """Get the group profile
+    """
+    PATTERNS = client_v2_patterns("/groups/(?P<group_id>[^/]*)/profile$")
+
+    def __init__(self, hs):
+        super(GroupServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        group_description = yield self.groups_handler.get_group_profile(group_id, user_id)
+
+        defer.returnValue((200, group_description))
+
+    @defer.inlineCallbacks
+    def on_POST(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        yield self.groups_handler.update_group_profile(
+            group_id, user_id, content,
+        )
+
+        defer.returnValue((200, {}))
+
+
+class GroupSummaryServlet(RestServlet):
+    """Get the full group summary
+    """
+    PATTERNS = client_v2_patterns("/groups/(?P<group_id>[^/]*)/summary$")
+
+    def __init__(self, hs):
+        super(GroupSummaryServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        get_group_summary = yield self.groups_handler.get_group_summary(group_id, user_id)
+
+        defer.returnValue((200, get_group_summary))
+
+
+class GroupSummaryRoomsCatServlet(RestServlet):
+    """Update/delete a rooms entry in the summary.
+
+    Matches both:
+        - /groups/:group/summary/rooms/:room_id
+        - /groups/:group/summary/categories/:category/rooms/:room_id
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/summary"
+        "(/categories/(?P<category_id>[^/]+))?"
+        "/rooms/(?P<room_id>[^/]*)$"
+    )
+
+    def __init__(self, hs):
+        super(GroupSummaryRoomsCatServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id, category_id, room_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        resp = yield self.groups_handler.update_group_summary_room(
+            group_id, user_id,
+            room_id=room_id,
+            category_id=category_id,
+            content=content,
+        )
+
+        defer.returnValue((200, resp))
+
+    @defer.inlineCallbacks
+    def on_DELETE(self, request, group_id, category_id, room_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        resp = yield self.groups_handler.delete_group_summary_room(
+            group_id, user_id,
+            room_id=room_id,
+            category_id=category_id,
+        )
+
+        defer.returnValue((200, resp))
+
+
+class GroupCategoryServlet(RestServlet):
+    """Get/add/update/delete a group category
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/categories/(?P<category_id>[^/]+)$"
+    )
+
+    def __init__(self, hs):
+        super(GroupCategoryServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id, category_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        category = yield self.groups_handler.get_group_category(
+            group_id, user_id,
+            category_id=category_id,
+        )
+
+        defer.returnValue((200, category))
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id, category_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        resp = yield self.groups_handler.update_group_category(
+            group_id, user_id,
+            category_id=category_id,
+            content=content,
+        )
+
+        defer.returnValue((200, resp))
+
+    @defer.inlineCallbacks
+    def on_DELETE(self, request, group_id, category_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        resp = yield self.groups_handler.delete_group_category(
+            group_id, user_id,
+            category_id=category_id,
+        )
+
+        defer.returnValue((200, resp))
+
+
+class GroupCategoriesServlet(RestServlet):
+    """Get all group categories
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/categories/$"
+    )
+
+    def __init__(self, hs):
+        super(GroupCategoriesServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        category = yield self.groups_handler.get_group_categories(
+            group_id, user_id,
+        )
+
+        defer.returnValue((200, category))
+
+
+class GroupRoleServlet(RestServlet):
+    """Get/add/update/delete a group role
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/roles/(?P<role_id>[^/]+)$"
+    )
+
+    def __init__(self, hs):
+        super(GroupRoleServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id, role_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        category = yield self.groups_handler.get_group_role(
+            group_id, user_id,
+            role_id=role_id,
+        )
+
+        defer.returnValue((200, category))
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id, role_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        resp = yield self.groups_handler.update_group_role(
+            group_id, user_id,
+            role_id=role_id,
+            content=content,
+        )
+
+        defer.returnValue((200, resp))
+
+    @defer.inlineCallbacks
+    def on_DELETE(self, request, group_id, role_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        resp = yield self.groups_handler.delete_group_role(
+            group_id, user_id,
+            role_id=role_id,
+        )
+
+        defer.returnValue((200, resp))
+
+
+class GroupRolesServlet(RestServlet):
+    """Get all group roles
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/roles/$"
+    )
+
+    def __init__(self, hs):
+        super(GroupRolesServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        category = yield self.groups_handler.get_group_roles(
+            group_id, user_id,
+        )
+
+        defer.returnValue((200, category))
+
+
+class GroupSummaryUsersRoleServlet(RestServlet):
+    """Update/delete a user's entry in the summary.
+
+    Matches both:
+        - /groups/:group/summary/users/:room_id
+        - /groups/:group/summary/roles/:role/users/:user_id
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/summary"
+        "(/roles/(?P<role_id>[^/]+))?"
+        "/users/(?P<user_id>[^/]*)$"
+    )
+
+    def __init__(self, hs):
+        super(GroupSummaryUsersRoleServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id, role_id, user_id):
+        requester = yield self.auth.get_user_by_req(request)
+        requester_user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        resp = yield self.groups_handler.update_group_summary_user(
+            group_id, requester_user_id,
+            user_id=user_id,
+            role_id=role_id,
+            content=content,
+        )
+
+        defer.returnValue((200, resp))
+
+    @defer.inlineCallbacks
+    def on_DELETE(self, request, group_id, role_id, user_id):
+        requester = yield self.auth.get_user_by_req(request)
+        requester_user_id = requester.user.to_string()
+
+        resp = yield self.groups_handler.delete_group_summary_user(
+            group_id, requester_user_id,
+            user_id=user_id,
+            role_id=role_id,
+        )
+
+        defer.returnValue((200, resp))
+
+
+class GroupRoomServlet(RestServlet):
+    """Get all rooms in a group
+    """
+    PATTERNS = client_v2_patterns("/groups/(?P<group_id>[^/]*)/rooms$")
+
+    def __init__(self, hs):
+        super(GroupRoomServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        result = yield self.groups_handler.get_rooms_in_group(group_id, user_id)
+
+        defer.returnValue((200, result))
+
+
+class GroupUsersServlet(RestServlet):
+    """Get all users in a group
+    """
+    PATTERNS = client_v2_patterns("/groups/(?P<group_id>[^/]*)/users$")
+
+    def __init__(self, hs):
+        super(GroupUsersServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        result = yield self.groups_handler.get_users_in_group(group_id, user_id)
+
+        defer.returnValue((200, result))
+
+
+class GroupInvitedUsersServlet(RestServlet):
+    """Get users invited to a group
+    """
+    PATTERNS = client_v2_patterns("/groups/(?P<group_id>[^/]*)/invited_users$")
+
+    def __init__(self, hs):
+        super(GroupInvitedUsersServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        result = yield self.groups_handler.get_invited_users_in_group(group_id, user_id)
+
+        defer.returnValue((200, result))
+
+
+class GroupCreateServlet(RestServlet):
+    """Create a group
+    """
+    PATTERNS = client_v2_patterns("/create_group$")
+
+    def __init__(self, hs):
+        super(GroupCreateServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+        self.server_name = hs.hostname
+
+    @defer.inlineCallbacks
+    def on_POST(self, request):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        # TODO: Create group on remote server
+        content = parse_json_object_from_request(request)
+        localpart = content.pop("localpart")
+        group_id = GroupID.create(localpart, self.server_name).to_string()
+
+        result = yield self.groups_handler.create_group(group_id, user_id, content)
+
+        defer.returnValue((200, result))
+
+
+class GroupAdminRoomsServlet(RestServlet):
+    """Add a room to the group
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/admin/rooms/(?P<room_id>[^/]*)$"
+    )
+
+    def __init__(self, hs):
+        super(GroupAdminRoomsServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id, room_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        result = yield self.groups_handler.add_room_to_group(
+            group_id, user_id, room_id, content,
+        )
+
+        defer.returnValue((200, result))
+
+    @defer.inlineCallbacks
+    def on_DELETE(self, request, group_id, room_id):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        result = yield self.groups_handler.remove_room_from_group(
+            group_id, user_id, room_id,
+        )
+
+        defer.returnValue((200, result))
+
+
+class GroupAdminUsersInviteServlet(RestServlet):
+    """Invite a user to the group
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/admin/users/invite/(?P<user_id>[^/]*)$"
+    )
+
+    def __init__(self, hs):
+        super(GroupAdminUsersInviteServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+        self.store = hs.get_datastore()
+        self.is_mine_id = hs.is_mine_id
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id, user_id):
+        requester = yield self.auth.get_user_by_req(request)
+        requester_user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        config = content.get("config", {})
+        result = yield self.groups_handler.invite(
+            group_id, user_id, requester_user_id, config,
+        )
+
+        defer.returnValue((200, result))
+
+
+class GroupAdminUsersKickServlet(RestServlet):
+    """Kick a user from the group
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/admin/users/remove/(?P<user_id>[^/]*)$"
+    )
+
+    def __init__(self, hs):
+        super(GroupAdminUsersKickServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id, user_id):
+        requester = yield self.auth.get_user_by_req(request)
+        requester_user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        result = yield self.groups_handler.remove_user_from_group(
+            group_id, user_id, requester_user_id, content,
+        )
+
+        defer.returnValue((200, result))
+
+
+class GroupSelfLeaveServlet(RestServlet):
+    """Leave a joined group
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/self/leave$"
+    )
+
+    def __init__(self, hs):
+        super(GroupSelfLeaveServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        requester_user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        result = yield self.groups_handler.remove_user_from_group(
+            group_id, requester_user_id, requester_user_id, content,
+        )
+
+        defer.returnValue((200, result))
+
+
+class GroupSelfJoinServlet(RestServlet):
+    """Attempt to join a group, or knock
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/self/join$"
+    )
+
+    def __init__(self, hs):
+        super(GroupSelfJoinServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        requester_user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        result = yield self.groups_handler.join_group(
+            group_id, requester_user_id, content,
+        )
+
+        defer.returnValue((200, result))
+
+
+class GroupSelfAcceptInviteServlet(RestServlet):
+    """Accept a group invite
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/self/accept_invite$"
+    )
+
+    def __init__(self, hs):
+        super(GroupSelfAcceptInviteServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        requester_user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        result = yield self.groups_handler.accept_invite(
+            group_id, requester_user_id, content,
+        )
+
+        defer.returnValue((200, result))
+
+
+class GroupSelfUpdatePublicityServlet(RestServlet):
+    """Update whether we publicise a users membership of a group
+    """
+    PATTERNS = client_v2_patterns(
+        "/groups/(?P<group_id>[^/]*)/self/update_publicity$"
+    )
+
+    def __init__(self, hs):
+        super(GroupSelfUpdatePublicityServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.store = hs.get_datastore()
+
+    @defer.inlineCallbacks
+    def on_PUT(self, request, group_id):
+        requester = yield self.auth.get_user_by_req(request)
+        requester_user_id = requester.user.to_string()
+
+        content = parse_json_object_from_request(request)
+        publicise = content["publicise"]
+        yield self.store.update_group_publicity(
+            group_id, requester_user_id, publicise,
+        )
+
+        defer.returnValue((200, {}))
+
+
+class PublicisedGroupsForUserServlet(RestServlet):
+    """Get the list of groups a user is advertising
+    """
+    PATTERNS = client_v2_patterns(
+        "/publicised_groups/(?P<user_id>[^/]*)$"
+    )
+
+    def __init__(self, hs):
+        super(PublicisedGroupsForUserServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.store = hs.get_datastore()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request, user_id):
+        yield self.auth.get_user_by_req(request)
+
+        result = yield self.groups_handler.get_publicised_groups_for_user(
+            user_id
+        )
+
+        defer.returnValue((200, result))
+
+
+class PublicisedGroupsForUsersServlet(RestServlet):
+    """Get the list of groups a user is advertising
+    """
+    PATTERNS = client_v2_patterns(
+        "/publicised_groups$"
+    )
+
+    def __init__(self, hs):
+        super(PublicisedGroupsForUsersServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.store = hs.get_datastore()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_POST(self, request):
+        yield self.auth.get_user_by_req(request)
+
+        content = parse_json_object_from_request(request)
+        user_ids = content["user_ids"]
+
+        result = yield self.groups_handler.bulk_get_publicised_groups(
+            user_ids
+        )
+
+        defer.returnValue((200, result))
+
+
+class GroupsForUserServlet(RestServlet):
+    """Get all groups the logged in user is joined to
+    """
+    PATTERNS = client_v2_patterns(
+        "/joined_groups$"
+    )
+
+    def __init__(self, hs):
+        super(GroupsForUserServlet, self).__init__()
+        self.auth = hs.get_auth()
+        self.clock = hs.get_clock()
+        self.groups_handler = hs.get_groups_local_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request):
+        requester = yield self.auth.get_user_by_req(request)
+        user_id = requester.user.to_string()
+
+        result = yield self.groups_handler.get_joined_groups(user_id)
+
+        defer.returnValue((200, result))
+
+
+def register_servlets(hs, http_server):
+    GroupServlet(hs).register(http_server)
+    GroupSummaryServlet(hs).register(http_server)
+    GroupInvitedUsersServlet(hs).register(http_server)
+    GroupUsersServlet(hs).register(http_server)
+    GroupRoomServlet(hs).register(http_server)
+    GroupCreateServlet(hs).register(http_server)
+    GroupAdminRoomsServlet(hs).register(http_server)
+    GroupAdminUsersInviteServlet(hs).register(http_server)
+    GroupAdminUsersKickServlet(hs).register(http_server)
+    GroupSelfLeaveServlet(hs).register(http_server)
+    GroupSelfJoinServlet(hs).register(http_server)
+    GroupSelfAcceptInviteServlet(hs).register(http_server)
+    GroupsForUserServlet(hs).register(http_server)
+    GroupCategoryServlet(hs).register(http_server)
+    GroupCategoriesServlet(hs).register(http_server)
+    GroupSummaryRoomsCatServlet(hs).register(http_server)
+    GroupRoleServlet(hs).register(http_server)
+    GroupRolesServlet(hs).register(http_server)
+    GroupSelfUpdatePublicityServlet(hs).register(http_server)
+    GroupSummaryUsersRoleServlet(hs).register(http_server)
+    PublicisedGroupsForUserServlet(hs).register(http_server)
+    PublicisedGroupsForUsersServlet(hs).register(http_server)
diff --git a/synapse/rest/client/v2_alpha/register.py b/synapse/rest/client/v2_alpha/register.py
index 1421c18152..d9a8cdbbb5 100644
--- a/synapse/rest/client/v2_alpha/register.py
+++ b/synapse/rest/client/v2_alpha/register.py
@@ -17,8 +17,10 @@
 from twisted.internet import defer
 
 import synapse
+import synapse.types
 from synapse.api.auth import get_access_token_from_request, has_access_token
 from synapse.api.constants import LoginType
+from synapse.types import RoomID, RoomAlias
 from synapse.api.errors import SynapseError, Codes, UnrecognizedRequestError
 from synapse.http.servlet import (
     RestServlet, parse_json_object_from_request, assert_params_in_request, parse_string
@@ -170,6 +172,7 @@ class RegisterRestServlet(RestServlet):
         self.auth_handler = hs.get_auth_handler()
         self.registration_handler = hs.get_handlers().registration_handler
         self.identity_handler = hs.get_handlers().identity_handler
+        self.room_member_handler = hs.get_handlers().room_member_handler
         self.device_handler = hs.get_device_handler()
         self.macaroon_gen = hs.get_macaroon_generator()
 
@@ -340,6 +343,14 @@ class RegisterRestServlet(RestServlet):
                 generate_token=False,
             )
 
+            # auto-join the user to any rooms we're supposed to dump them into
+            fake_requester = synapse.types.create_requester(registered_user_id)
+            for r in self.hs.config.auto_join_rooms:
+                try:
+                    yield self._join_user_to_room(fake_requester, r)
+                except Exception as e:
+                    logger.error("Failed to join new user to %r: %r", r, e)
+
             # remember that we've now registered that user account, and with
             #  what user ID (since the user may not have specified)
             self.auth_handler.set_session_data(
@@ -373,6 +384,29 @@ class RegisterRestServlet(RestServlet):
         return 200, {}
 
     @defer.inlineCallbacks
+    def _join_user_to_room(self, requester, room_identifier):
+        room_id = None
+        if RoomID.is_valid(room_identifier):
+            room_id = room_identifier
+        elif RoomAlias.is_valid(room_identifier):
+            room_alias = RoomAlias.from_string(room_identifier)
+            room_id, remote_room_hosts = (
+                yield self.room_member_handler.lookup_room_alias(room_alias)
+            )
+            room_id = room_id.to_string()
+        else:
+            raise SynapseError(400, "%s was not legal room ID or room alias" % (
+                room_identifier,
+            ))
+
+        yield self.room_member_handler.update_membership(
+            requester=requester,
+            target=requester.user,
+            room_id=room_id,
+            action="join",
+        )
+
+    @defer.inlineCallbacks
     def _do_appservice_registration(self, username, as_token, body):
         user_id = yield self.registration_handler.appservice_register(
             username, as_token
diff --git a/synapse/rest/client/v2_alpha/sync.py b/synapse/rest/client/v2_alpha/sync.py
index 978af9c280..a1e0e53b33 100644
--- a/synapse/rest/client/v2_alpha/sync.py
+++ b/synapse/rest/client/v2_alpha/sync.py
@@ -200,6 +200,11 @@ class SyncRestServlet(RestServlet):
                 "invite": invited,
                 "leave": archived,
             },
+            "groups": {
+                "join": sync_result.groups.join,
+                "invite": sync_result.groups.invite,
+                "leave": sync_result.groups.leave,
+            },
             "device_one_time_keys_count": sync_result.device_one_time_keys_count,
             "next_batch": sync_result.next_batch.to_string(),
         }
diff --git a/synapse/rest/media/v1/filepath.py b/synapse/rest/media/v1/filepath.py
index d92b7ff337..d5164e47e0 100644
--- a/synapse/rest/media/v1/filepath.py
+++ b/synapse/rest/media/v1/filepath.py
@@ -14,78 +14,200 @@
 # limitations under the License.
 
 import os
+import re
+import functools
+
+NEW_FORMAT_ID_RE = re.compile(r"^\d\d\d\d-\d\d-\d\d")
+
+
+def _wrap_in_base_path(func):
+    """Takes a function that returns a relative path and turns it into an
+    absolute path based on the location of the primary media store
+    """
+    @functools.wraps(func)
+    def _wrapped(self, *args, **kwargs):
+        path = func(self, *args, **kwargs)
+        return os.path.join(self.base_path, path)
+
+    return _wrapped
 
 
 class MediaFilePaths(object):
+    """Describes where files are stored on disk.
 
-    def __init__(self, base_path):
-        self.base_path = base_path
+    Most of the functions have a `*_rel` variant which returns a file path that
+    is relative to the base media store path. This is mainly used when we want
+    to write to the backup media store (when one is configured)
+    """
 
-    def default_thumbnail(self, default_top_level, default_sub_type, width,
-                          height, content_type, method):
+    def __init__(self, primary_base_path):
+        self.base_path = primary_base_path
+
+    def default_thumbnail_rel(self, default_top_level, default_sub_type, width,
+                              height, content_type, method):
         top_level_type, sub_type = content_type.split("/")
         file_name = "%i-%i-%s-%s-%s" % (
             width, height, top_level_type, sub_type, method
         )
         return os.path.join(
-            self.base_path, "default_thumbnails", default_top_level,
+            "default_thumbnails", default_top_level,
             default_sub_type, file_name
         )
 
-    def local_media_filepath(self, media_id):
+    default_thumbnail = _wrap_in_base_path(default_thumbnail_rel)
+
+    def local_media_filepath_rel(self, media_id):
         return os.path.join(
-            self.base_path, "local_content",
+            "local_content",
             media_id[0:2], media_id[2:4], media_id[4:]
         )
 
-    def local_media_thumbnail(self, media_id, width, height, content_type,
-                              method):
+    local_media_filepath = _wrap_in_base_path(local_media_filepath_rel)
+
+    def local_media_thumbnail_rel(self, media_id, width, height, content_type,
+                                  method):
         top_level_type, sub_type = content_type.split("/")
         file_name = "%i-%i-%s-%s-%s" % (
             width, height, top_level_type, sub_type, method
         )
         return os.path.join(
-            self.base_path, "local_thumbnails",
+            "local_thumbnails",
             media_id[0:2], media_id[2:4], media_id[4:],
             file_name
         )
 
-    def remote_media_filepath(self, server_name, file_id):
+    local_media_thumbnail = _wrap_in_base_path(local_media_thumbnail_rel)
+
+    def remote_media_filepath_rel(self, server_name, file_id):
         return os.path.join(
-            self.base_path, "remote_content", server_name,
+            "remote_content", server_name,
             file_id[0:2], file_id[2:4], file_id[4:]
         )
 
-    def remote_media_thumbnail(self, server_name, file_id, width, height,
-                               content_type, method):
+    remote_media_filepath = _wrap_in_base_path(remote_media_filepath_rel)
+
+    def remote_media_thumbnail_rel(self, server_name, file_id, width, height,
+                                   content_type, method):
         top_level_type, sub_type = content_type.split("/")
         file_name = "%i-%i-%s-%s" % (width, height, top_level_type, sub_type)
         return os.path.join(
-            self.base_path, "remote_thumbnail", server_name,
+            "remote_thumbnail", server_name,
             file_id[0:2], file_id[2:4], file_id[4:],
             file_name
         )
 
+    remote_media_thumbnail = _wrap_in_base_path(remote_media_thumbnail_rel)
+
     def remote_media_thumbnail_dir(self, server_name, file_id):
         return os.path.join(
             self.base_path, "remote_thumbnail", server_name,
             file_id[0:2], file_id[2:4], file_id[4:],
         )
 
-    def url_cache_filepath(self, media_id):
-        return os.path.join(
-            self.base_path, "url_cache",
-            media_id[0:2], media_id[2:4], media_id[4:]
-        )
+    def url_cache_filepath_rel(self, media_id):
+        if NEW_FORMAT_ID_RE.match(media_id):
+            # Media id is of the form <DATE><RANDOM_STRING>
+            # E.g.: 2017-09-28-fsdRDt24DS234dsf
+            return os.path.join(
+                "url_cache",
+                media_id[:10], media_id[11:]
+            )
+        else:
+            return os.path.join(
+                "url_cache",
+                media_id[0:2], media_id[2:4], media_id[4:],
+            )
+
+    url_cache_filepath = _wrap_in_base_path(url_cache_filepath_rel)
+
+    def url_cache_filepath_dirs_to_delete(self, media_id):
+        "The dirs to try and remove if we delete the media_id file"
+        if NEW_FORMAT_ID_RE.match(media_id):
+            return [
+                os.path.join(
+                    self.base_path, "url_cache",
+                    media_id[:10],
+                ),
+            ]
+        else:
+            return [
+                os.path.join(
+                    self.base_path, "url_cache",
+                    media_id[0:2], media_id[2:4],
+                ),
+                os.path.join(
+                    self.base_path, "url_cache",
+                    media_id[0:2],
+                ),
+            ]
+
+    def url_cache_thumbnail_rel(self, media_id, width, height, content_type,
+                                method):
+        # Media id is of the form <DATE><RANDOM_STRING>
+        # E.g.: 2017-09-28-fsdRDt24DS234dsf
 
-    def url_cache_thumbnail(self, media_id, width, height, content_type,
-                            method):
         top_level_type, sub_type = content_type.split("/")
         file_name = "%i-%i-%s-%s-%s" % (
             width, height, top_level_type, sub_type, method
         )
-        return os.path.join(
-            self.base_path, "url_cache_thumbnails",
-            media_id[0:2], media_id[2:4], media_id[4:],
-            file_name
-        )
+
+        if NEW_FORMAT_ID_RE.match(media_id):
+            return os.path.join(
+                "url_cache_thumbnails",
+                media_id[:10], media_id[11:],
+                file_name
+            )
+        else:
+            return os.path.join(
+                "url_cache_thumbnails",
+                media_id[0:2], media_id[2:4], media_id[4:],
+                file_name
+            )
+
+    url_cache_thumbnail = _wrap_in_base_path(url_cache_thumbnail_rel)
+
+    def url_cache_thumbnail_directory(self, media_id):
+        # Media id is of the form <DATE><RANDOM_STRING>
+        # E.g.: 2017-09-28-fsdRDt24DS234dsf
+
+        if NEW_FORMAT_ID_RE.match(media_id):
+            return os.path.join(
+                self.base_path, "url_cache_thumbnails",
+                media_id[:10], media_id[11:],
+            )
+        else:
+            return os.path.join(
+                self.base_path, "url_cache_thumbnails",
+                media_id[0:2], media_id[2:4], media_id[4:],
+            )
+
+    def url_cache_thumbnail_dirs_to_delete(self, media_id):
+        "The dirs to try and remove if we delete the media_id thumbnails"
+        # Media id is of the form <DATE><RANDOM_STRING>
+        # E.g.: 2017-09-28-fsdRDt24DS234dsf
+        if NEW_FORMAT_ID_RE.match(media_id):
+            return [
+                os.path.join(
+                    self.base_path, "url_cache_thumbnails",
+                    media_id[:10], media_id[11:],
+                ),
+                os.path.join(
+                    self.base_path, "url_cache_thumbnails",
+                    media_id[:10],
+                ),
+            ]
+        else:
+            return [
+                os.path.join(
+                    self.base_path, "url_cache_thumbnails",
+                    media_id[0:2], media_id[2:4], media_id[4:],
+                ),
+                os.path.join(
+                    self.base_path, "url_cache_thumbnails",
+                    media_id[0:2], media_id[2:4],
+                ),
+                os.path.join(
+                    self.base_path, "url_cache_thumbnails",
+                    media_id[0:2],
+                ),
+            ]
diff --git a/synapse/rest/media/v1/media_repository.py b/synapse/rest/media/v1/media_repository.py
index 0ea1248ce6..6b50b45b1f 100644
--- a/synapse/rest/media/v1/media_repository.py
+++ b/synapse/rest/media/v1/media_repository.py
@@ -33,7 +33,7 @@ from synapse.api.errors import SynapseError, HttpResponseException, \
 
 from synapse.util.async import Linearizer
 from synapse.util.stringutils import is_ascii
-from synapse.util.logcontext import preserve_context_over_fn
+from synapse.util.logcontext import make_deferred_yieldable, preserve_fn
 from synapse.util.retryutils import NotRetryingDestination
 
 import os
@@ -59,7 +59,14 @@ class MediaRepository(object):
         self.store = hs.get_datastore()
         self.max_upload_size = hs.config.max_upload_size
         self.max_image_pixels = hs.config.max_image_pixels
-        self.filepaths = MediaFilePaths(hs.config.media_store_path)
+
+        self.primary_base_path = hs.config.media_store_path
+        self.filepaths = MediaFilePaths(self.primary_base_path)
+
+        self.backup_base_path = hs.config.backup_media_store_path
+
+        self.synchronous_backup_media_store = hs.config.synchronous_backup_media_store
+
         self.dynamic_thumbnails = hs.config.dynamic_thumbnails
         self.thumbnail_requirements = hs.config.thumbnail_requirements
 
@@ -87,18 +94,86 @@ class MediaRepository(object):
         if not os.path.exists(dirname):
             os.makedirs(dirname)
 
+    @staticmethod
+    def _write_file_synchronously(source, fname):
+        """Write `source` to the path `fname` synchronously. Should be called
+        from a thread.
+
+        Args:
+            source: A file like object to be written
+            fname (str): Path to write to
+        """
+        MediaRepository._makedirs(fname)
+        source.seek(0)  # Ensure we read from the start of the file
+        with open(fname, "wb") as f:
+            shutil.copyfileobj(source, f)
+
+    @defer.inlineCallbacks
+    def write_to_file_and_backup(self, source, path):
+        """Write `source` to the on disk media store, and also the backup store
+        if configured.
+
+        Args:
+            source: A file like object that should be written
+            path (str): Relative path to write file to
+
+        Returns:
+            Deferred[str]: the file path written to in the primary media store
+        """
+        fname = os.path.join(self.primary_base_path, path)
+
+        # Write to the main repository
+        yield make_deferred_yieldable(threads.deferToThread(
+            self._write_file_synchronously, source, fname,
+        ))
+
+        # Write to backup repository
+        yield self.copy_to_backup(path)
+
+        defer.returnValue(fname)
+
+    @defer.inlineCallbacks
+    def copy_to_backup(self, path):
+        """Copy a file from the primary to backup media store, if configured.
+
+        Args:
+            path(str): Relative path to write file to
+        """
+        if self.backup_base_path:
+            primary_fname = os.path.join(self.primary_base_path, path)
+            backup_fname = os.path.join(self.backup_base_path, path)
+
+            # We can either wait for successful writing to the backup repository
+            # or write in the background and immediately return
+            if self.synchronous_backup_media_store:
+                yield make_deferred_yieldable(threads.deferToThread(
+                    shutil.copyfile, primary_fname, backup_fname,
+                ))
+            else:
+                preserve_fn(threads.deferToThread)(
+                    shutil.copyfile, primary_fname, backup_fname,
+                )
+
     @defer.inlineCallbacks
     def create_content(self, media_type, upload_name, content, content_length,
                        auth_user):
+        """Store uploaded content for a local user and return the mxc URL
+
+        Args:
+            media_type(str): The content type of the file
+            upload_name(str): The name of the file
+            content: A file like object that is the content to store
+            content_length(int): The length of the content
+            auth_user(str): The user_id of the uploader
+
+        Returns:
+            Deferred[str]: The mxc url of the stored content
+        """
         media_id = random_string(24)
 
-        fname = self.filepaths.local_media_filepath(media_id)
-        self._makedirs(fname)
-
-        # This shouldn't block for very long because the content will have
-        # already been uploaded at this point.
-        with open(fname, "wb") as f:
-            f.write(content)
+        fname = yield self.write_to_file_and_backup(
+            content, self.filepaths.local_media_filepath_rel(media_id)
+        )
 
         logger.info("Stored local media in file %r", fname)
 
@@ -115,7 +190,7 @@ class MediaRepository(object):
             "media_length": content_length,
         }
 
-        yield self._generate_local_thumbnails(media_id, media_info)
+        yield self._generate_thumbnails(None, media_id, media_info)
 
         defer.returnValue("mxc://%s/%s" % (self.server_name, media_id))
 
@@ -148,9 +223,10 @@ class MediaRepository(object):
     def _download_remote_file(self, server_name, media_id):
         file_id = random_string(24)
 
-        fname = self.filepaths.remote_media_filepath(
+        fpath = self.filepaths.remote_media_filepath_rel(
             server_name, file_id
         )
+        fname = os.path.join(self.primary_base_path, fpath)
         self._makedirs(fname)
 
         try:
@@ -192,6 +268,8 @@ class MediaRepository(object):
                                      server_name, media_id)
                     raise SynapseError(502, "Failed to fetch remote media")
 
+            yield self.copy_to_backup(fpath)
+
             media_type = headers["Content-Type"][0]
             time_now_ms = self.clock.time_msec()
 
@@ -244,7 +322,7 @@ class MediaRepository(object):
             "filesystem_id": file_id,
         }
 
-        yield self._generate_remote_thumbnails(
+        yield self._generate_thumbnails(
             server_name, media_id, media_info
         )
 
@@ -253,9 +331,8 @@ class MediaRepository(object):
     def _get_thumbnail_requirements(self, media_type):
         return self.thumbnail_requirements.get(media_type, ())
 
-    def _generate_thumbnail(self, input_path, t_path, t_width, t_height,
+    def _generate_thumbnail(self, thumbnailer, t_width, t_height,
                             t_method, t_type):
-        thumbnailer = Thumbnailer(input_path)
         m_width = thumbnailer.width
         m_height = thumbnailer.height
 
@@ -267,72 +344,105 @@ class MediaRepository(object):
             return
 
         if t_method == "crop":
-            t_len = thumbnailer.crop(t_path, t_width, t_height, t_type)
+            t_byte_source = thumbnailer.crop(t_width, t_height, t_type)
         elif t_method == "scale":
             t_width, t_height = thumbnailer.aspect(t_width, t_height)
             t_width = min(m_width, t_width)
             t_height = min(m_height, t_height)
-            t_len = thumbnailer.scale(t_path, t_width, t_height, t_type)
+            t_byte_source = thumbnailer.scale(t_width, t_height, t_type)
         else:
-            t_len = None
+            t_byte_source = None
 
-        return t_len
+        return t_byte_source
 
     @defer.inlineCallbacks
     def generate_local_exact_thumbnail(self, media_id, t_width, t_height,
                                        t_method, t_type):
         input_path = self.filepaths.local_media_filepath(media_id)
 
-        t_path = self.filepaths.local_media_thumbnail(
-            media_id, t_width, t_height, t_type, t_method
-        )
-        self._makedirs(t_path)
-
-        t_len = yield preserve_context_over_fn(
-            threads.deferToThread,
+        thumbnailer = Thumbnailer(input_path)
+        t_byte_source = yield make_deferred_yieldable(threads.deferToThread(
             self._generate_thumbnail,
-            input_path, t_path, t_width, t_height, t_method, t_type
-        )
+            thumbnailer, t_width, t_height, t_method, t_type
+        ))
+
+        if t_byte_source:
+            try:
+                output_path = yield self.write_to_file_and_backup(
+                    t_byte_source,
+                    self.filepaths.local_media_thumbnail_rel(
+                        media_id, t_width, t_height, t_type, t_method
+                    )
+                )
+            finally:
+                t_byte_source.close()
+
+            logger.info("Stored thumbnail in file %r", output_path)
+
+            t_len = os.path.getsize(output_path)
 
-        if t_len:
             yield self.store.store_local_thumbnail(
                 media_id, t_width, t_height, t_type, t_method, t_len
             )
 
-            defer.returnValue(t_path)
+            defer.returnValue(output_path)
 
     @defer.inlineCallbacks
     def generate_remote_exact_thumbnail(self, server_name, file_id, media_id,
                                         t_width, t_height, t_method, t_type):
         input_path = self.filepaths.remote_media_filepath(server_name, file_id)
 
-        t_path = self.filepaths.remote_media_thumbnail(
-            server_name, file_id, t_width, t_height, t_type, t_method
-        )
-        self._makedirs(t_path)
-
-        t_len = yield preserve_context_over_fn(
-            threads.deferToThread,
+        thumbnailer = Thumbnailer(input_path)
+        t_byte_source = yield make_deferred_yieldable(threads.deferToThread(
             self._generate_thumbnail,
-            input_path, t_path, t_width, t_height, t_method, t_type
-        )
+            thumbnailer, t_width, t_height, t_method, t_type
+        ))
+
+        if t_byte_source:
+            try:
+                output_path = yield self.write_to_file_and_backup(
+                    t_byte_source,
+                    self.filepaths.remote_media_thumbnail_rel(
+                        server_name, file_id, t_width, t_height, t_type, t_method
+                    )
+                )
+            finally:
+                t_byte_source.close()
+
+            logger.info("Stored thumbnail in file %r", output_path)
+
+            t_len = os.path.getsize(output_path)
 
-        if t_len:
             yield self.store.store_remote_media_thumbnail(
                 server_name, media_id, file_id,
                 t_width, t_height, t_type, t_method, t_len
             )
 
-            defer.returnValue(t_path)
+            defer.returnValue(output_path)
 
     @defer.inlineCallbacks
-    def _generate_local_thumbnails(self, media_id, media_info, url_cache=False):
+    def _generate_thumbnails(self, server_name, media_id, media_info, url_cache=False):
+        """Generate and store thumbnails for an image.
+
+        Args:
+            server_name(str|None): The server name if remote media, else None if local
+            media_id(str)
+            media_info(dict)
+            url_cache(bool): If we are thumbnailing images downloaded for the URL cache,
+                used exclusively by the url previewer
+
+        Returns:
+            Deferred[dict]: Dict with "width" and "height" keys of original image
+        """
         media_type = media_info["media_type"]
+        file_id = media_info.get("filesystem_id")
         requirements = self._get_thumbnail_requirements(media_type)
         if not requirements:
             return
 
-        if url_cache:
+        if server_name:
+            input_path = self.filepaths.remote_media_filepath(server_name, file_id)
+        elif url_cache:
             input_path = self.filepaths.url_cache_filepath(media_id)
         else:
             input_path = self.filepaths.local_media_filepath(media_id)
@@ -348,135 +458,72 @@ class MediaRepository(object):
             )
             return
 
-        local_thumbnails = []
-
-        def generate_thumbnails():
-            scales = set()
-            crops = set()
-            for r_width, r_height, r_method, r_type in requirements:
-                if r_method == "scale":
-                    t_width, t_height = thumbnailer.aspect(r_width, r_height)
-                    scales.add((
-                        min(m_width, t_width), min(m_height, t_height), r_type,
-                    ))
-                elif r_method == "crop":
-                    crops.add((r_width, r_height, r_type))
-
-            for t_width, t_height, t_type in scales:
-                t_method = "scale"
-                if url_cache:
-                    t_path = self.filepaths.url_cache_thumbnail(
-                        media_id, t_width, t_height, t_type, t_method
-                    )
-                else:
-                    t_path = self.filepaths.local_media_thumbnail(
-                        media_id, t_width, t_height, t_type, t_method
-                    )
-                self._makedirs(t_path)
-                t_len = thumbnailer.scale(t_path, t_width, t_height, t_type)
+        # We deduplicate the thumbnail sizes by ignoring the cropped versions if
+        # they have the same dimensions of a scaled one.
+        thumbnails = {}
+        for r_width, r_height, r_method, r_type in requirements:
+            if r_method == "crop":
+                thumbnails.setdefault((r_width, r_height, r_type), r_method)
+            elif r_method == "scale":
+                t_width, t_height = thumbnailer.aspect(r_width, r_height)
+                t_width = min(m_width, t_width)
+                t_height = min(m_height, t_height)
+                thumbnails[(t_width, t_height, r_type)] = r_method
+
+        # Now we generate the thumbnails for each dimension, store it
+        for (t_width, t_height, t_type), t_method in thumbnails.iteritems():
+            # Work out the correct file name for thumbnail
+            if server_name:
+                file_path = self.filepaths.remote_media_thumbnail_rel(
+                    server_name, file_id, t_width, t_height, t_type, t_method
+                )
+            elif url_cache:
+                file_path = self.filepaths.url_cache_thumbnail_rel(
+                    media_id, t_width, t_height, t_type, t_method
+                )
+            else:
+                file_path = self.filepaths.local_media_thumbnail_rel(
+                    media_id, t_width, t_height, t_type, t_method
+                )
 
-                local_thumbnails.append((
-                    media_id, t_width, t_height, t_type, t_method, t_len
+            # Generate the thumbnail
+            if t_method == "crop":
+                t_byte_source = yield make_deferred_yieldable(threads.deferToThread(
+                    thumbnailer.crop,
+                    t_width, t_height, t_type,
                 ))
-
-            for t_width, t_height, t_type in crops:
-                if (t_width, t_height, t_type) in scales:
-                    # If the aspect ratio of the cropped thumbnail matches a purely
-                    # scaled one then there is no point in calculating a separate
-                    # thumbnail.
-                    continue
-                t_method = "crop"
-                if url_cache:
-                    t_path = self.filepaths.url_cache_thumbnail(
-                        media_id, t_width, t_height, t_type, t_method
-                    )
-                else:
-                    t_path = self.filepaths.local_media_thumbnail(
-                        media_id, t_width, t_height, t_type, t_method
-                    )
-                self._makedirs(t_path)
-                t_len = thumbnailer.crop(t_path, t_width, t_height, t_type)
-                local_thumbnails.append((
-                    media_id, t_width, t_height, t_type, t_method, t_len
+            elif t_method == "scale":
+                t_byte_source = yield make_deferred_yieldable(threads.deferToThread(
+                    thumbnailer.scale,
+                    t_width, t_height, t_type,
                 ))
+            else:
+                logger.error("Unrecognized method: %r", t_method)
+                continue
 
-        yield preserve_context_over_fn(threads.deferToThread, generate_thumbnails)
-
-        for l in local_thumbnails:
-            yield self.store.store_local_thumbnail(*l)
-
-        defer.returnValue({
-            "width": m_width,
-            "height": m_height,
-        })
-
-    @defer.inlineCallbacks
-    def _generate_remote_thumbnails(self, server_name, media_id, media_info):
-        media_type = media_info["media_type"]
-        file_id = media_info["filesystem_id"]
-        requirements = self._get_thumbnail_requirements(media_type)
-        if not requirements:
-            return
+            if not t_byte_source:
+                continue
 
-        remote_thumbnails = []
+            try:
+                # Write to disk
+                output_path = yield self.write_to_file_and_backup(
+                    t_byte_source, file_path,
+                )
+            finally:
+                t_byte_source.close()
 
-        input_path = self.filepaths.remote_media_filepath(server_name, file_id)
-        thumbnailer = Thumbnailer(input_path)
-        m_width = thumbnailer.width
-        m_height = thumbnailer.height
+            t_len = os.path.getsize(output_path)
 
-        def generate_thumbnails():
-            if m_width * m_height >= self.max_image_pixels:
-                logger.info(
-                    "Image too large to thumbnail %r x %r > %r",
-                    m_width, m_height, self.max_image_pixels
-                )
-                return
-
-            scales = set()
-            crops = set()
-            for r_width, r_height, r_method, r_type in requirements:
-                if r_method == "scale":
-                    t_width, t_height = thumbnailer.aspect(r_width, r_height)
-                    scales.add((
-                        min(m_width, t_width), min(m_height, t_height), r_type,
-                    ))
-                elif r_method == "crop":
-                    crops.add((r_width, r_height, r_type))
-
-            for t_width, t_height, t_type in scales:
-                t_method = "scale"
-                t_path = self.filepaths.remote_media_thumbnail(
-                    server_name, file_id, t_width, t_height, t_type, t_method
-                )
-                self._makedirs(t_path)
-                t_len = thumbnailer.scale(t_path, t_width, t_height, t_type)
-                remote_thumbnails.append([
+            # Write to database
+            if server_name:
+                yield self.store.store_remote_media_thumbnail(
                     server_name, media_id, file_id,
                     t_width, t_height, t_type, t_method, t_len
-                ])
-
-            for t_width, t_height, t_type in crops:
-                if (t_width, t_height, t_type) in scales:
-                    # If the aspect ratio of the cropped thumbnail matches a purely
-                    # scaled one then there is no point in calculating a separate
-                    # thumbnail.
-                    continue
-                t_method = "crop"
-                t_path = self.filepaths.remote_media_thumbnail(
-                    server_name, file_id, t_width, t_height, t_type, t_method
                 )
-                self._makedirs(t_path)
-                t_len = thumbnailer.crop(t_path, t_width, t_height, t_type)
-                remote_thumbnails.append([
-                    server_name, media_id, file_id,
-                    t_width, t_height, t_type, t_method, t_len
-                ])
-
-        yield preserve_context_over_fn(threads.deferToThread, generate_thumbnails)
-
-        for r in remote_thumbnails:
-            yield self.store.store_remote_media_thumbnail(*r)
+            else:
+                yield self.store.store_local_thumbnail(
+                    media_id, t_width, t_height, t_type, t_method, t_len
+                )
 
         defer.returnValue({
             "width": m_width,
@@ -497,6 +544,8 @@ class MediaRepository(object):
 
             logger.info("Deleting: %r", key)
 
+            # TODO: Should we delete from the backup store
+
             with (yield self.remote_media_linearizer.queue(key)):
                 full_path = self.filepaths.remote_media_filepath(origin, file_id)
                 try:
diff --git a/synapse/rest/media/v1/preview_url_resource.py b/synapse/rest/media/v1/preview_url_resource.py
index b81a336c5d..2a3e37fdf4 100644
--- a/synapse/rest/media/v1/preview_url_resource.py
+++ b/synapse/rest/media/v1/preview_url_resource.py
@@ -36,6 +36,9 @@ import cgi
 import ujson as json
 import urlparse
 import itertools
+import datetime
+import errno
+import shutil
 
 import logging
 logger = logging.getLogger(__name__)
@@ -56,6 +59,7 @@ class PreviewUrlResource(Resource):
         self.store = hs.get_datastore()
         self.client = SpiderHttpClient(hs)
         self.media_repo = media_repo
+        self.primary_base_path = media_repo.primary_base_path
 
         self.url_preview_url_blacklist = hs.config.url_preview_url_blacklist
 
@@ -70,6 +74,10 @@ class PreviewUrlResource(Resource):
 
         self.downloads = {}
 
+        self._cleaner_loop = self.clock.looping_call(
+            self._expire_url_cache_data, 10 * 1000
+        )
+
     def render_GET(self, request):
         self._async_render_GET(request)
         return NOT_DONE_YET
@@ -130,7 +138,7 @@ class PreviewUrlResource(Resource):
         cache_result = yield self.store.get_url_cache(url, ts)
         if (
             cache_result and
-            cache_result["download_ts"] + cache_result["expires"] > ts and
+            cache_result["expires_ts"] > ts and
             cache_result["response_code"] / 100 == 2
         ):
             respond_with_json_bytes(
@@ -163,8 +171,8 @@ class PreviewUrlResource(Resource):
         logger.debug("got media_info of '%s'" % media_info)
 
         if _is_media(media_info['media_type']):
-            dims = yield self.media_repo._generate_local_thumbnails(
-                media_info['filesystem_id'], media_info, url_cache=True,
+            dims = yield self.media_repo._generate_thumbnails(
+                None, media_info['filesystem_id'], media_info, url_cache=True,
             )
 
             og = {
@@ -209,8 +217,8 @@ class PreviewUrlResource(Resource):
 
                 if _is_media(image_info['media_type']):
                     # TODO: make sure we don't choke on white-on-transparent images
-                    dims = yield self.media_repo._generate_local_thumbnails(
-                        image_info['filesystem_id'], image_info, url_cache=True,
+                    dims = yield self.media_repo._generate_thumbnails(
+                        None, image_info['filesystem_id'], image_info, url_cache=True,
                     )
                     if dims:
                         og["og:image:width"] = dims['width']
@@ -239,7 +247,7 @@ class PreviewUrlResource(Resource):
             url,
             media_info["response_code"],
             media_info["etag"],
-            media_info["expires"],
+            media_info["expires"] + media_info["created_ts"],
             json.dumps(og),
             media_info["filesystem_id"],
             media_info["created_ts"],
@@ -253,10 +261,10 @@ class PreviewUrlResource(Resource):
         # we're most likely being explicitly triggered by a human rather than a
         # bot, so are we really a robot?
 
-        # XXX: horrible duplication with base_resource's _download_remote_file()
-        file_id = random_string(24)
+        file_id = datetime.date.today().isoformat() + '_' + random_string(16)
 
-        fname = self.filepaths.url_cache_filepath(file_id)
+        fpath = self.filepaths.url_cache_filepath_rel(file_id)
+        fname = os.path.join(self.primary_base_path, fpath)
         self.media_repo._makedirs(fname)
 
         try:
@@ -267,6 +275,8 @@ class PreviewUrlResource(Resource):
                 )
                 # FIXME: pass through 404s and other error messages nicely
 
+            yield self.media_repo.copy_to_backup(fpath)
+
             media_type = headers["Content-Type"][0]
             time_now_ms = self.clock.time_msec()
 
@@ -328,6 +338,91 @@ class PreviewUrlResource(Resource):
             "etag": headers["ETag"][0] if "ETag" in headers else None,
         })
 
+    @defer.inlineCallbacks
+    def _expire_url_cache_data(self):
+        """Clean up expired url cache content, media and thumbnails.
+        """
+
+        # TODO: Delete from backup media store
+
+        now = self.clock.time_msec()
+
+        # First we delete expired url cache entries
+        media_ids = yield self.store.get_expired_url_cache(now)
+
+        removed_media = []
+        for media_id in media_ids:
+            fname = self.filepaths.url_cache_filepath(media_id)
+            try:
+                os.remove(fname)
+            except OSError as e:
+                # If the path doesn't exist, meh
+                if e.errno != errno.ENOENT:
+                    logger.warn("Failed to remove media: %r: %s", media_id, e)
+                    continue
+
+            removed_media.append(media_id)
+
+            try:
+                dirs = self.filepaths.url_cache_filepath_dirs_to_delete(media_id)
+                for dir in dirs:
+                    os.rmdir(dir)
+            except:
+                pass
+
+        yield self.store.delete_url_cache(removed_media)
+
+        if removed_media:
+            logger.info("Deleted %d entries from url cache", len(removed_media))
+
+        # Now we delete old images associated with the url cache.
+        # These may be cached for a bit on the client (i.e., they
+        # may have a room open with a preview url thing open).
+        # So we wait a couple of days before deleting, just in case.
+        expire_before = now - 2 * 24 * 60 * 60 * 1000
+        media_ids = yield self.store.get_url_cache_media_before(expire_before)
+
+        removed_media = []
+        for media_id in media_ids:
+            fname = self.filepaths.url_cache_filepath(media_id)
+            try:
+                os.remove(fname)
+            except OSError as e:
+                # If the path doesn't exist, meh
+                if e.errno != errno.ENOENT:
+                    logger.warn("Failed to remove media: %r: %s", media_id, e)
+                    continue
+
+            try:
+                dirs = self.filepaths.url_cache_filepath_dirs_to_delete(media_id)
+                for dir in dirs:
+                    os.rmdir(dir)
+            except:
+                pass
+
+            thumbnail_dir = self.filepaths.url_cache_thumbnail_directory(media_id)
+            try:
+                shutil.rmtree(thumbnail_dir)
+            except OSError as e:
+                # If the path doesn't exist, meh
+                if e.errno != errno.ENOENT:
+                    logger.warn("Failed to remove media: %r: %s", media_id, e)
+                    continue
+
+            removed_media.append(media_id)
+
+            try:
+                dirs = self.filepaths.url_cache_thumbnail_dirs_to_delete(media_id)
+                for dir in dirs:
+                    os.rmdir(dir)
+            except:
+                pass
+
+        yield self.store.delete_url_cache_media(removed_media)
+
+        if removed_media:
+            logger.info("Deleted %d media from url cache", len(removed_media))
+
 
 def decode_and_calc_og(body, media_uri, request_encoding=None):
     from lxml import etree
diff --git a/synapse/rest/media/v1/thumbnailer.py b/synapse/rest/media/v1/thumbnailer.py
index 3868d4f65f..e1ee535b9a 100644
--- a/synapse/rest/media/v1/thumbnailer.py
+++ b/synapse/rest/media/v1/thumbnailer.py
@@ -50,12 +50,16 @@ class Thumbnailer(object):
         else:
             return ((max_height * self.width) // self.height, max_height)
 
-    def scale(self, output_path, width, height, output_type):
-        """Rescales the image to the given dimensions"""
+    def scale(self, width, height, output_type):
+        """Rescales the image to the given dimensions.
+
+        Returns:
+            BytesIO: the bytes of the encoded image ready to be written to disk
+        """
         scaled = self.image.resize((width, height), Image.ANTIALIAS)
-        return self.save_image(scaled, output_type, output_path)
+        return self._encode_image(scaled, output_type)
 
-    def crop(self, output_path, width, height, output_type):
+    def crop(self, width, height, output_type):
         """Rescales and crops the image to the given dimensions preserving
         aspect::
             (w_in / h_in) = (w_scaled / h_scaled)
@@ -65,6 +69,9 @@ class Thumbnailer(object):
         Args:
             max_width: The largest possible width.
             max_height: The larget possible height.
+
+        Returns:
+            BytesIO: the bytes of the encoded image ready to be written to disk
         """
         if width * self.height > height * self.width:
             scaled_height = (width * self.height) // self.width
@@ -82,13 +89,9 @@ class Thumbnailer(object):
             crop_left = (scaled_width - width) // 2
             crop_right = width + crop_left
             cropped = scaled_image.crop((crop_left, 0, crop_right, height))
-        return self.save_image(cropped, output_type, output_path)
+        return self._encode_image(cropped, output_type)
 
-    def save_image(self, output_image, output_type, output_path):
+    def _encode_image(self, output_image, output_type):
         output_bytes_io = BytesIO()
         output_image.save(output_bytes_io, self.FORMATS[output_type], quality=80)
-        output_bytes = output_bytes_io.getvalue()
-        with open(output_path, "wb") as output_file:
-            output_file.write(output_bytes)
-        logger.info("Stored thumbnail in file %r", output_path)
-        return len(output_bytes)
+        return output_bytes_io
diff --git a/synapse/rest/media/v1/upload_resource.py b/synapse/rest/media/v1/upload_resource.py
index 4ab33f73bf..f6f498cdc5 100644
--- a/synapse/rest/media/v1/upload_resource.py
+++ b/synapse/rest/media/v1/upload_resource.py
@@ -93,7 +93,7 @@ class UploadResource(Resource):
         # TODO(markjh): parse content-dispostion
 
         content_uri = yield self.media_repo.create_content(
-            media_type, upload_name, request.content.read(),
+            media_type, upload_name, request.content,
             content_length, requester.user
         )