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-rw-r--r--synapse/storage/database.py4
-rw-r--r--synapse/storage/databases/main/devices.py7
-rw-r--r--synapse/storage/databases/main/media_repository.py57
-rw-r--r--synapse/storage/databases/main/purge_events.py2
-rw-r--r--synapse/storage/databases/main/push_rule.py131
-rw-r--r--synapse/storage/databases/main/schema/delta/58/07add_method_to_thumbnail_constraint.sql.postgres33
-rw-r--r--synapse/storage/databases/main/schema/delta/58/07add_method_to_thumbnail_constraint.sql.sqlite44
-rw-r--r--synapse/storage/databases/main/schema/delta/58/10_pushrules_enabled_delete_obsolete.sql28
-rw-r--r--synapse/storage/databases/main/schema/delta/58/15_catchup_destination_rooms.sql42
-rw-r--r--synapse/storage/databases/main/schema/delta/58/16populate_stats_process_rooms_fix.sql22
-rw-r--r--synapse/storage/databases/main/schema/delta/58/17_catchup_last_successful.sql21
-rw-r--r--synapse/storage/databases/main/stats.py36
-rw-r--r--synapse/storage/databases/main/stream.py21
-rw-r--r--synapse/storage/databases/main/transactions.py104
-rw-r--r--synapse/storage/prepare_database.py26
-rw-r--r--synapse/storage/util/id_generators.py43
16 files changed, 550 insertions, 71 deletions
diff --git a/synapse/storage/database.py b/synapse/storage/database.py
index ed8a9bffb1..79ec8f119d 100644
--- a/synapse/storage/database.py
+++ b/synapse/storage/database.py
@@ -952,7 +952,7 @@ class DatabasePool:
         key_names: Collection[str],
         key_values: Collection[Iterable[Any]],
         value_names: Collection[str],
-        value_values: Iterable[Iterable[str]],
+        value_values: Iterable[Iterable[Any]],
     ) -> None:
         """
         Upsert, many times.
@@ -981,7 +981,7 @@ class DatabasePool:
         key_names: Iterable[str],
         key_values: Collection[Iterable[Any]],
         value_names: Collection[str],
-        value_values: Iterable[Iterable[str]],
+        value_values: Iterable[Iterable[Any]],
     ) -> None:
         """
         Upsert, many times, but without native UPSERT support or batching.
diff --git a/synapse/storage/databases/main/devices.py b/synapse/storage/databases/main/devices.py
index add4e3ea0e..306fc6947c 100644
--- a/synapse/storage/databases/main/devices.py
+++ b/synapse/storage/databases/main/devices.py
@@ -481,7 +481,7 @@ class DeviceWorkerStore(SQLBaseStore):
         }
 
     async def get_users_whose_devices_changed(
-        self, from_key: str, user_ids: Iterable[str]
+        self, from_key: int, user_ids: Iterable[str]
     ) -> Set[str]:
         """Get set of users whose devices have changed since `from_key` that
         are in the given list of user_ids.
@@ -493,7 +493,6 @@ class DeviceWorkerStore(SQLBaseStore):
         Returns:
             The set of user_ids whose devices have changed since `from_key`
         """
-        from_key = int(from_key)
 
         # Get set of users who *may* have changed. Users not in the returned
         # list have definitely not changed.
@@ -527,7 +526,7 @@ class DeviceWorkerStore(SQLBaseStore):
         )
 
     async def get_users_whose_signatures_changed(
-        self, user_id: str, from_key: str
+        self, user_id: str, from_key: int
     ) -> Set[str]:
         """Get the users who have new cross-signing signatures made by `user_id` since
         `from_key`.
@@ -539,7 +538,7 @@ class DeviceWorkerStore(SQLBaseStore):
         Returns:
             A set of user IDs with updated signatures.
         """
-        from_key = int(from_key)
+
         if self._user_signature_stream_cache.has_entity_changed(user_id, from_key):
             sql = """
                 SELECT DISTINCT user_ids FROM user_signature_stream
diff --git a/synapse/storage/databases/main/media_repository.py b/synapse/storage/databases/main/media_repository.py
index 86557d5512..1d76c761a6 100644
--- a/synapse/storage/databases/main/media_repository.py
+++ b/synapse/storage/databases/main/media_repository.py
@@ -17,6 +17,10 @@ from typing import Any, Dict, Iterable, List, Optional, Tuple
 from synapse.storage._base import SQLBaseStore
 from synapse.storage.database import DatabasePool
 
+BG_UPDATE_REMOVE_MEDIA_REPO_INDEX_WITHOUT_METHOD = (
+    "media_repository_drop_index_wo_method"
+)
+
 
 class MediaRepositoryBackgroundUpdateStore(SQLBaseStore):
     def __init__(self, database: DatabasePool, db_conn, hs):
@@ -32,6 +36,59 @@ class MediaRepositoryBackgroundUpdateStore(SQLBaseStore):
             where_clause="url_cache IS NOT NULL",
         )
 
+        # The following the updates add the method to the unique constraint of
+        # the thumbnail databases. That fixes an issue, where thumbnails of the
+        # same resolution, but different methods could overwrite one another.
+        # This can happen with custom thumbnail configs or with dynamic thumbnailing.
+        self.db_pool.updates.register_background_index_update(
+            update_name="local_media_repository_thumbnails_method_idx",
+            index_name="local_media_repository_thumbn_media_id_width_height_method_key",
+            table="local_media_repository_thumbnails",
+            columns=[
+                "media_id",
+                "thumbnail_width",
+                "thumbnail_height",
+                "thumbnail_type",
+                "thumbnail_method",
+            ],
+            unique=True,
+        )
+
+        self.db_pool.updates.register_background_index_update(
+            update_name="remote_media_repository_thumbnails_method_idx",
+            index_name="remote_media_repository_thumbn_media_origin_id_width_height_method_key",
+            table="remote_media_cache_thumbnails",
+            columns=[
+                "media_origin",
+                "media_id",
+                "thumbnail_width",
+                "thumbnail_height",
+                "thumbnail_type",
+                "thumbnail_method",
+            ],
+            unique=True,
+        )
+
+        self.db_pool.updates.register_background_update_handler(
+            BG_UPDATE_REMOVE_MEDIA_REPO_INDEX_WITHOUT_METHOD,
+            self._drop_media_index_without_method,
+        )
+
+    async def _drop_media_index_without_method(self, progress, batch_size):
+        def f(txn):
+            txn.execute(
+                "ALTER TABLE local_media_repository_thumbnails DROP CONSTRAINT IF EXISTS local_media_repository_thumbn_media_id_thumbnail_width_thum_key"
+            )
+            txn.execute(
+                "ALTER TABLE remote_media_cache_thumbnails DROP CONSTRAINT IF EXISTS remote_media_repository_thumbn_media_id_thumbnail_width_thum_key"
+            )
+
+        await self.db_pool.runInteraction("drop_media_indices_without_method", f)
+        await self.db_pool.updates._end_background_update(
+            BG_UPDATE_REMOVE_MEDIA_REPO_INDEX_WITHOUT_METHOD
+        )
+        return 1
+
 
 class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
     """Persistence for attachments and avatars"""
diff --git a/synapse/storage/databases/main/purge_events.py b/synapse/storage/databases/main/purge_events.py
index ea833829ae..d7a03cbf7d 100644
--- a/synapse/storage/databases/main/purge_events.py
+++ b/synapse/storage/databases/main/purge_events.py
@@ -69,6 +69,7 @@ class PurgeEventsStore(StateGroupWorkerStore, SQLBaseStore):
         #     room_depth
         #     state_groups
         #     state_groups_state
+        #     destination_rooms
 
         # we will build a temporary table listing the events so that we don't
         # have to keep shovelling the list back and forth across the
@@ -336,6 +337,7 @@ class PurgeEventsStore(StateGroupWorkerStore, SQLBaseStore):
         # and finally, the tables with an index on room_id (or no useful index)
         for table in (
             "current_state_events",
+            "destination_rooms",
             "event_backward_extremities",
             "event_forward_extremities",
             "event_json",
diff --git a/synapse/storage/databases/main/push_rule.py b/synapse/storage/databases/main/push_rule.py
index 0de802a86b..9790a31998 100644
--- a/synapse/storage/databases/main/push_rule.py
+++ b/synapse/storage/databases/main/push_rule.py
@@ -13,11 +13,11 @@
 # 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 abc
 import logging
 from typing import List, Tuple, Union
 
+from synapse.api.errors import NotFoundError, StoreError
 from synapse.push.baserules import list_with_base_rules
 from synapse.replication.slave.storage._slaved_id_tracker import SlavedIdTracker
 from synapse.storage._base import SQLBaseStore, db_to_json
@@ -27,6 +27,7 @@ from synapse.storage.databases.main.events_worker import EventsWorkerStore
 from synapse.storage.databases.main.pusher import PusherWorkerStore
 from synapse.storage.databases.main.receipts import ReceiptsWorkerStore
 from synapse.storage.databases.main.roommember import RoomMemberWorkerStore
+from synapse.storage.engines import PostgresEngine, Sqlite3Engine
 from synapse.storage.push_rule import InconsistentRuleException, RuleNotFoundException
 from synapse.storage.util.id_generators import StreamIdGenerator
 from synapse.util import json_encoder
@@ -540,6 +541,25 @@ class PushRuleStore(PushRulesWorkerStore):
                 },
             )
 
+        # ensure we have a push_rules_enable row
+        # enabledness defaults to true
+        if isinstance(self.database_engine, PostgresEngine):
+            sql = """
+                INSERT INTO push_rules_enable (id, user_name, rule_id, enabled)
+                VALUES (?, ?, ?, ?)
+                ON CONFLICT DO NOTHING
+            """
+        elif isinstance(self.database_engine, Sqlite3Engine):
+            sql = """
+                INSERT OR IGNORE INTO push_rules_enable (id, user_name, rule_id, enabled)
+                VALUES (?, ?, ?, ?)
+            """
+        else:
+            raise RuntimeError("Unknown database engine")
+
+        new_enable_id = self._push_rules_enable_id_gen.get_next()
+        txn.execute(sql, (new_enable_id, user_id, rule_id, 1))
+
     async def delete_push_rule(self, user_id: str, rule_id: str) -> None:
         """
         Delete a push rule. Args specify the row to be deleted and can be
@@ -552,6 +572,12 @@ class PushRuleStore(PushRulesWorkerStore):
         """
 
         def delete_push_rule_txn(txn, stream_id, event_stream_ordering):
+            # we don't use simple_delete_one_txn because that would fail if the
+            # user did not have a push_rule_enable row.
+            self.db_pool.simple_delete_txn(
+                txn, "push_rules_enable", {"user_name": user_id, "rule_id": rule_id}
+            )
+
             self.db_pool.simple_delete_one_txn(
                 txn, "push_rules", {"user_name": user_id, "rule_id": rule_id}
             )
@@ -570,10 +596,29 @@ class PushRuleStore(PushRulesWorkerStore):
                 event_stream_ordering,
             )
 
-    async def set_push_rule_enabled(self, user_id, rule_id, enabled) -> None:
+    async def set_push_rule_enabled(
+        self, user_id: str, rule_id: str, enabled: bool, is_default_rule: bool
+    ) -> None:
+        """
+        Sets the `enabled` state of a push rule.
+
+        Args:
+            user_id: the user ID of the user who wishes to enable/disable the rule
+                e.g. '@tina:example.org'
+            rule_id: the full rule ID of the rule to be enabled/disabled
+                e.g. 'global/override/.m.rule.roomnotif'
+                  or 'global/override/myCustomRule'
+            enabled: True if the rule is to be enabled, False if it is to be
+                disabled
+            is_default_rule: True if and only if this is a server-default rule.
+                This skips the check for existence (as only user-created rules
+                are always stored in the database `push_rules` table).
+
+        Raises:
+            NotFoundError if the rule does not exist.
+        """
         with await self._push_rules_stream_id_gen.get_next() as stream_id:
             event_stream_ordering = self._stream_id_gen.get_current_token()
-
             await self.db_pool.runInteraction(
                 "_set_push_rule_enabled_txn",
                 self._set_push_rule_enabled_txn,
@@ -582,12 +627,47 @@ class PushRuleStore(PushRulesWorkerStore):
                 user_id,
                 rule_id,
                 enabled,
+                is_default_rule,
             )
 
     def _set_push_rule_enabled_txn(
-        self, txn, stream_id, event_stream_ordering, user_id, rule_id, enabled
+        self,
+        txn,
+        stream_id,
+        event_stream_ordering,
+        user_id,
+        rule_id,
+        enabled,
+        is_default_rule,
     ):
         new_id = self._push_rules_enable_id_gen.get_next()
+
+        if not is_default_rule:
+            # first check it exists; we need to lock for key share so that a
+            # transaction that deletes the push rule will conflict with this one.
+            # We also need a push_rule_enable row to exist for every push_rules
+            # row, otherwise it is possible to simultaneously delete a push rule
+            # (that has no _enable row) and enable it, resulting in a dangling
+            # _enable row. To solve this: we either need to use SERIALISABLE or
+            # ensure we always have a push_rule_enable row for every push_rule
+            # row. We chose the latter.
+            for_key_share = "FOR KEY SHARE"
+            if not isinstance(self.database_engine, PostgresEngine):
+                # For key share is not applicable/available on SQLite
+                for_key_share = ""
+            sql = (
+                """
+                SELECT 1 FROM push_rules
+                WHERE user_name = ? AND rule_id = ?
+                %s
+            """
+                % for_key_share
+            )
+            txn.execute(sql, (user_id, rule_id))
+            if txn.fetchone() is None:
+                # needed to set NOT_FOUND code.
+                raise NotFoundError("Push rule does not exist.")
+
         self.db_pool.simple_upsert_txn(
             txn,
             "push_rules_enable",
@@ -606,8 +686,30 @@ class PushRuleStore(PushRulesWorkerStore):
         )
 
     async def set_push_rule_actions(
-        self, user_id, rule_id, actions, is_default_rule
+        self,
+        user_id: str,
+        rule_id: str,
+        actions: List[Union[dict, str]],
+        is_default_rule: bool,
     ) -> None:
+        """
+        Sets the `actions` state of a push rule.
+
+        Will throw NotFoundError if the rule does not exist; the Code for this
+        is NOT_FOUND.
+
+        Args:
+            user_id: the user ID of the user who wishes to enable/disable the rule
+                e.g. '@tina:example.org'
+            rule_id: the full rule ID of the rule to be enabled/disabled
+                e.g. 'global/override/.m.rule.roomnotif'
+                  or 'global/override/myCustomRule'
+            actions: A list of actions (each action being a dict or string),
+                e.g. ["notify", {"set_tweak": "highlight", "value": false}]
+            is_default_rule: True if and only if this is a server-default rule.
+                This skips the check for existence (as only user-created rules
+                are always stored in the database `push_rules` table).
+        """
         actions_json = json_encoder.encode(actions)
 
         def set_push_rule_actions_txn(txn, stream_id, event_stream_ordering):
@@ -629,12 +731,19 @@ class PushRuleStore(PushRulesWorkerStore):
                     update_stream=False,
                 )
             else:
-                self.db_pool.simple_update_one_txn(
-                    txn,
-                    "push_rules",
-                    {"user_name": user_id, "rule_id": rule_id},
-                    {"actions": actions_json},
-                )
+                try:
+                    self.db_pool.simple_update_one_txn(
+                        txn,
+                        "push_rules",
+                        {"user_name": user_id, "rule_id": rule_id},
+                        {"actions": actions_json},
+                    )
+                except StoreError as serr:
+                    if serr.code == 404:
+                        # this sets the NOT_FOUND error Code
+                        raise NotFoundError("Push rule does not exist")
+                    else:
+                        raise
 
             self._insert_push_rules_update_txn(
                 txn,
diff --git a/synapse/storage/databases/main/schema/delta/58/07add_method_to_thumbnail_constraint.sql.postgres b/synapse/storage/databases/main/schema/delta/58/07add_method_to_thumbnail_constraint.sql.postgres
new file mode 100644
index 0000000000..b64926e9c9
--- /dev/null
+++ b/synapse/storage/databases/main/schema/delta/58/07add_method_to_thumbnail_constraint.sql.postgres
@@ -0,0 +1,33 @@
+/* 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.
+ */
+
+/*
+ * This adds the method to the unique key constraint of the thumbnail databases.
+ * Otherwise you can't have a scaled and a cropped thumbnail with the same
+ * resolution, which happens quite often with dynamic thumbnailing.
+ * This is the postgres specific migration modifying the table with a background
+ * migration.
+ */
+
+-- add new index that includes method to local media
+INSERT INTO background_updates (update_name, progress_json) VALUES
+  ('local_media_repository_thumbnails_method_idx', '{}');
+
+-- add new index that includes method to remote media
+INSERT INTO background_updates (update_name, progress_json, depends_on) VALUES
+  ('remote_media_repository_thumbnails_method_idx', '{}', 'local_media_repository_thumbnails_method_idx');
+
+-- drop old index
+INSERT INTO background_updates (update_name, progress_json, depends_on) VALUES
+  ('media_repository_drop_index_wo_method', '{}', 'remote_media_repository_thumbnails_method_idx');
+
diff --git a/synapse/storage/databases/main/schema/delta/58/07add_method_to_thumbnail_constraint.sql.sqlite b/synapse/storage/databases/main/schema/delta/58/07add_method_to_thumbnail_constraint.sql.sqlite
new file mode 100644
index 0000000000..1d0c04b53a
--- /dev/null
+++ b/synapse/storage/databases/main/schema/delta/58/07add_method_to_thumbnail_constraint.sql.sqlite
@@ -0,0 +1,44 @@
+/* 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.
+ */
+
+/*
+ * This adds the method to the unique key constraint of the thumbnail databases.
+ * Otherwise you can't have a scaled and a cropped thumbnail with the same
+ * resolution, which happens quite often with dynamic thumbnailing.
+ * This is a sqlite specific migration, since sqlite can't modify the unique
+ * constraint of a table without recreating it.
+ */
+
+CREATE TABLE local_media_repository_thumbnails_new ( media_id TEXT, thumbnail_width INTEGER, thumbnail_height INTEGER, thumbnail_type TEXT, thumbnail_method TEXT, thumbnail_length INTEGER, UNIQUE ( media_id, thumbnail_width, thumbnail_height, thumbnail_type, thumbnail_method ) );
+
+INSERT INTO local_media_repository_thumbnails_new
+    SELECT media_id, thumbnail_width, thumbnail_height, thumbnail_type, thumbnail_method, thumbnail_length
+    FROM local_media_repository_thumbnails;
+
+DROP TABLE local_media_repository_thumbnails;
+
+ALTER TABLE local_media_repository_thumbnails_new RENAME TO local_media_repository_thumbnails;
+
+CREATE INDEX local_media_repository_thumbnails_media_id ON local_media_repository_thumbnails (media_id);
+
+
+
+CREATE TABLE IF NOT EXISTS remote_media_cache_thumbnails_new ( media_origin TEXT, media_id TEXT, thumbnail_width INTEGER, thumbnail_height INTEGER, thumbnail_method TEXT, thumbnail_type TEXT, thumbnail_length INTEGER, filesystem_id TEXT, UNIQUE ( media_origin, media_id, thumbnail_width, thumbnail_height, thumbnail_type, thumbnail_method ) );
+
+INSERT INTO remote_media_cache_thumbnails_new
+    SELECT media_origin, media_id, thumbnail_width, thumbnail_height, thumbnail_method, thumbnail_type, thumbnail_length, filesystem_id
+    FROM remote_media_cache_thumbnails;
+
+DROP TABLE remote_media_cache_thumbnails;
+
+ALTER TABLE remote_media_cache_thumbnails_new RENAME TO remote_media_cache_thumbnails;
diff --git a/synapse/storage/databases/main/schema/delta/58/10_pushrules_enabled_delete_obsolete.sql b/synapse/storage/databases/main/schema/delta/58/10_pushrules_enabled_delete_obsolete.sql
new file mode 100644
index 0000000000..847aebd85e
--- /dev/null
+++ b/synapse/storage/databases/main/schema/delta/58/10_pushrules_enabled_delete_obsolete.sql
@@ -0,0 +1,28 @@
+/* Copyright 2020 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.
+ */
+
+/**
+  Delete stuck 'enabled' bits that correspond to deleted or non-existent push rules.
+  We ignore rules that are server-default rules because they are not defined
+  in the `push_rules` table.
+**/
+
+DELETE FROM push_rules_enable WHERE
+  rule_id NOT LIKE 'global/%/.m.rule.%'
+  AND NOT EXISTS (
+    SELECT 1 FROM push_rules
+    WHERE push_rules.user_name = push_rules_enable.user_name
+      AND push_rules.rule_id = push_rules_enable.rule_id
+  );
diff --git a/synapse/storage/databases/main/schema/delta/58/15_catchup_destination_rooms.sql b/synapse/storage/databases/main/schema/delta/58/15_catchup_destination_rooms.sql
new file mode 100644
index 0000000000..ebfbed7925
--- /dev/null
+++ b/synapse/storage/databases/main/schema/delta/58/15_catchup_destination_rooms.sql
@@ -0,0 +1,42 @@
+/* Copyright 2020 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.
+ */
+-- This schema delta alters the schema to enable 'catching up' remote homeservers
+-- after there has been a connectivity problem for any reason.
+
+-- This stores, for each (destination, room) pair, the stream_ordering of the
+-- latest event for that destination.
+CREATE TABLE IF NOT EXISTS destination_rooms (
+  -- the destination in question.
+  destination TEXT NOT NULL REFERENCES destinations (destination),
+  -- the ID of the room in question
+  room_id TEXT NOT NULL REFERENCES rooms (room_id),
+  -- the stream_ordering of the event
+  stream_ordering BIGINT NOT NULL,
+  PRIMARY KEY (destination, room_id)
+  -- We don't declare a foreign key on stream_ordering here because that'd mean
+  -- we'd need to either maintain an index (expensive) or do a table scan of
+  -- destination_rooms whenever we delete an event (also potentially expensive).
+  -- In addition to that, a foreign key on stream_ordering would be redundant
+  -- as this row doesn't need to refer to a specific event; if the event gets
+  -- deleted then it doesn't affect the validity of the stream_ordering here.
+);
+
+-- This index is needed to make it so that a deletion of a room (in the rooms
+-- table) can be efficient, as otherwise a table scan would need to be performed
+-- to check that no destination_rooms rows point to the room to be deleted.
+-- Also: it makes it efficient to delete all the entries for a given room ID,
+-- such as when purging a room.
+CREATE INDEX IF NOT EXISTS destination_rooms_room_id
+    ON destination_rooms (room_id);
diff --git a/synapse/storage/databases/main/schema/delta/58/16populate_stats_process_rooms_fix.sql b/synapse/storage/databases/main/schema/delta/58/16populate_stats_process_rooms_fix.sql
new file mode 100644
index 0000000000..55f5d0f732
--- /dev/null
+++ b/synapse/storage/databases/main/schema/delta/58/16populate_stats_process_rooms_fix.sql
@@ -0,0 +1,22 @@
+/* Copyright 2020 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.
+ */
+-- This delta file fixes a regression introduced by 58/12room_stats.sql, removing the hacky
+-- populate_stats_process_rooms_2 background job and restores the functionality under the
+-- original name.
+-- See https://github.com/matrix-org/synapse/issues/8238 for details
+
+DELETE FROM background_updates WHERE update_name = 'populate_stats_process_rooms';
+UPDATE background_updates SET update_name = 'populate_stats_process_rooms'
+    WHERE update_name = 'populate_stats_process_rooms_2';
diff --git a/synapse/storage/databases/main/schema/delta/58/17_catchup_last_successful.sql b/synapse/storage/databases/main/schema/delta/58/17_catchup_last_successful.sql
new file mode 100644
index 0000000000..a67aa5e500
--- /dev/null
+++ b/synapse/storage/databases/main/schema/delta/58/17_catchup_last_successful.sql
@@ -0,0 +1,21 @@
+/* Copyright 2020 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.
+ */
+
+-- This column tracks the stream_ordering of the event that was most recently
+-- successfully transmitted to the destination.
+-- A value of NULL means that we have not sent an event successfully yet
+-- (at least, not since the introduction of this column).
+ALTER TABLE destinations
+    ADD COLUMN last_successful_stream_ordering BIGINT;
diff --git a/synapse/storage/databases/main/stats.py b/synapse/storage/databases/main/stats.py
index 55a250ef06..30840dbbaa 100644
--- a/synapse/storage/databases/main/stats.py
+++ b/synapse/storage/databases/main/stats.py
@@ -74,9 +74,6 @@ class StatsStore(StateDeltasStore):
             "populate_stats_process_rooms", self._populate_stats_process_rooms
         )
         self.db_pool.updates.register_background_update_handler(
-            "populate_stats_process_rooms_2", self._populate_stats_process_rooms_2
-        )
-        self.db_pool.updates.register_background_update_handler(
             "populate_stats_process_users", self._populate_stats_process_users
         )
         # we no longer need to perform clean-up, but we will give ourselves
@@ -148,31 +145,10 @@ class StatsStore(StateDeltasStore):
         return len(users_to_work_on)
 
     async def _populate_stats_process_rooms(self, progress, batch_size):
-        """
-        This was a background update which regenerated statistics for rooms.
-
-        It has been replaced by StatsStore._populate_stats_process_rooms_2. This background
-        job has been scheduled to run as part of Synapse v1.0.0, and again now. To ensure
-        someone upgrading from <v1.0.0, this background task has been turned into a no-op
-        so that the potentially expensive task is not run twice.
-
-        Further context: https://github.com/matrix-org/synapse/pull/7977
-        """
-        await self.db_pool.updates._end_background_update(
-            "populate_stats_process_rooms"
-        )
-        return 1
-
-    async def _populate_stats_process_rooms_2(self, progress, batch_size):
-        """
-        This is a background update which regenerates statistics for rooms.
-
-        It replaces StatsStore._populate_stats_process_rooms. See its docstring for the
-        reasoning.
-        """
+        """This is a background update which regenerates statistics for rooms."""
         if not self.stats_enabled:
             await self.db_pool.updates._end_background_update(
-                "populate_stats_process_rooms_2"
+                "populate_stats_process_rooms"
             )
             return 1
 
@@ -189,13 +165,13 @@ class StatsStore(StateDeltasStore):
             return [r for r, in txn]
 
         rooms_to_work_on = await self.db_pool.runInteraction(
-            "populate_stats_rooms_2_get_batch", _get_next_batch
+            "populate_stats_rooms_get_batch", _get_next_batch
         )
 
         # No more rooms -- complete the transaction.
         if not rooms_to_work_on:
             await self.db_pool.updates._end_background_update(
-                "populate_stats_process_rooms_2"
+                "populate_stats_process_rooms"
             )
             return 1
 
@@ -204,9 +180,9 @@ class StatsStore(StateDeltasStore):
             progress["last_room_id"] = room_id
 
         await self.db_pool.runInteraction(
-            "_populate_stats_process_rooms_2",
+            "_populate_stats_process_rooms",
             self.db_pool.updates._background_update_progress_txn,
-            "populate_stats_process_rooms_2",
+            "populate_stats_process_rooms",
             progress,
         )
 
diff --git a/synapse/storage/databases/main/stream.py b/synapse/storage/databases/main/stream.py
index be6df8a6d1..08a13a8b47 100644
--- a/synapse/storage/databases/main/stream.py
+++ b/synapse/storage/databases/main/stream.py
@@ -79,8 +79,8 @@ _EventDictReturn = namedtuple(
 def generate_pagination_where_clause(
     direction: str,
     column_names: Tuple[str, str],
-    from_token: Optional[Tuple[int, int]],
-    to_token: Optional[Tuple[int, int]],
+    from_token: Optional[Tuple[Optional[int], int]],
+    to_token: Optional[Tuple[Optional[int], int]],
     engine: BaseDatabaseEngine,
 ) -> str:
     """Creates an SQL expression to bound the columns by the pagination
@@ -535,13 +535,13 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         if limit == 0:
             return [], end_token
 
-        end_token = RoomStreamToken.parse(end_token)
+        parsed_end_token = RoomStreamToken.parse(end_token)
 
         rows, token = await self.db_pool.runInteraction(
             "get_recent_event_ids_for_room",
             self._paginate_room_events_txn,
             room_id,
-            from_token=end_token,
+            from_token=parsed_end_token,
             limit=limit,
         )
 
@@ -989,8 +989,8 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         bounds = generate_pagination_where_clause(
             direction=direction,
             column_names=("topological_ordering", "stream_ordering"),
-            from_token=from_token,
-            to_token=to_token,
+            from_token=from_token.as_tuple(),
+            to_token=to_token.as_tuple() if to_token else None,
             engine=self.database_engine,
         )
 
@@ -1083,16 +1083,17 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             and `to_key`).
         """
 
-        from_key = RoomStreamToken.parse(from_key)
+        parsed_from_key = RoomStreamToken.parse(from_key)
+        parsed_to_key = None
         if to_key:
-            to_key = RoomStreamToken.parse(to_key)
+            parsed_to_key = RoomStreamToken.parse(to_key)
 
         rows, token = await self.db_pool.runInteraction(
             "paginate_room_events",
             self._paginate_room_events_txn,
             room_id,
-            from_key,
-            to_key,
+            parsed_from_key,
+            parsed_to_key,
             direction,
             limit,
             event_filter,
diff --git a/synapse/storage/databases/main/transactions.py b/synapse/storage/databases/main/transactions.py
index 5b31aab700..c0a958252e 100644
--- a/synapse/storage/databases/main/transactions.py
+++ b/synapse/storage/databases/main/transactions.py
@@ -15,13 +15,14 @@
 
 import logging
 from collections import namedtuple
-from typing import Optional, Tuple
+from typing import Iterable, Optional, Tuple
 
 from canonicaljson import encode_canonical_json
 
 from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage._base import SQLBaseStore, db_to_json
-from synapse.storage.database import DatabasePool
+from synapse.storage.database import DatabasePool, LoggingTransaction
+from synapse.storage.engines import PostgresEngine, Sqlite3Engine
 from synapse.types import JsonDict
 from synapse.util.caches.expiringcache import ExpiringCache
 
@@ -164,7 +165,9 @@ class TransactionStore(SQLBaseStore):
             allow_none=True,
         )
 
-        if result and result["retry_last_ts"] > 0:
+        # check we have a row and retry_last_ts is not null or zero
+        # (retry_last_ts can't be negative)
+        if result and result["retry_last_ts"]:
             return result
         else:
             return None
@@ -273,3 +276,98 @@ class TransactionStore(SQLBaseStore):
         await self.db_pool.runInteraction(
             "_cleanup_transactions", _cleanup_transactions_txn
         )
+
+    async def store_destination_rooms_entries(
+        self, destinations: Iterable[str], room_id: str, stream_ordering: int,
+    ) -> None:
+        """
+        Updates or creates `destination_rooms` entries in batch for a single event.
+
+        Args:
+            destinations: list of destinations
+            room_id: the room_id of the event
+            stream_ordering: the stream_ordering of the event
+        """
+
+        return await self.db_pool.runInteraction(
+            "store_destination_rooms_entries",
+            self._store_destination_rooms_entries_txn,
+            destinations,
+            room_id,
+            stream_ordering,
+        )
+
+    def _store_destination_rooms_entries_txn(
+        self,
+        txn: LoggingTransaction,
+        destinations: Iterable[str],
+        room_id: str,
+        stream_ordering: int,
+    ) -> None:
+
+        # ensure we have a `destinations` row for this destination, as there is
+        # a foreign key constraint.
+        if isinstance(self.database_engine, PostgresEngine):
+            q = """
+                INSERT INTO destinations (destination)
+                    VALUES (?)
+                    ON CONFLICT DO NOTHING;
+            """
+        elif isinstance(self.database_engine, Sqlite3Engine):
+            q = """
+                INSERT OR IGNORE INTO destinations (destination)
+                    VALUES (?);
+            """
+        else:
+            raise RuntimeError("Unknown database engine")
+
+        txn.execute_batch(q, ((destination,) for destination in destinations))
+
+        rows = [(destination, room_id) for destination in destinations]
+
+        self.db_pool.simple_upsert_many_txn(
+            txn,
+            "destination_rooms",
+            ["destination", "room_id"],
+            rows,
+            ["stream_ordering"],
+            [(stream_ordering,)] * len(rows),
+        )
+
+    async def get_destination_last_successful_stream_ordering(
+        self, destination: str
+    ) -> Optional[int]:
+        """
+        Gets the stream ordering of the PDU most-recently successfully sent
+        to the specified destination, or None if this information has not been
+        tracked yet.
+
+        Args:
+            destination: the destination to query
+        """
+        return await self.db_pool.simple_select_one_onecol(
+            "destinations",
+            {"destination": destination},
+            "last_successful_stream_ordering",
+            allow_none=True,
+            desc="get_last_successful_stream_ordering",
+        )
+
+    async def set_destination_last_successful_stream_ordering(
+        self, destination: str, last_successful_stream_ordering: int
+    ) -> None:
+        """
+        Marks that we have successfully sent the PDUs up to and including the
+        one specified.
+
+        Args:
+            destination: the destination we have successfully sent to
+            last_successful_stream_ordering: the stream_ordering of the most
+                recent successfully-sent PDU
+        """
+        return await self.db_pool.simple_upsert(
+            "destinations",
+            keyvalues={"destination": destination},
+            values={"last_successful_stream_ordering": last_successful_stream_ordering},
+            desc="set_last_successful_stream_ordering",
+        )
diff --git a/synapse/storage/prepare_database.py b/synapse/storage/prepare_database.py
index ee60e2a718..a7f2dfb850 100644
--- a/synapse/storage/prepare_database.py
+++ b/synapse/storage/prepare_database.py
@@ -19,12 +19,15 @@ import logging
 import os
 import re
 from collections import Counter
-from typing import TextIO
+from typing import Optional, TextIO
 
 import attr
 
+from synapse.config.homeserver import HomeServerConfig
+from synapse.storage.engines import BaseDatabaseEngine
 from synapse.storage.engines.postgres import PostgresEngine
-from synapse.storage.types import Cursor
+from synapse.storage.types import Connection, Cursor
+from synapse.types import Collection
 
 logger = logging.getLogger(__name__)
 
@@ -63,7 +66,12 @@ UNAPPLIED_DELTA_ON_WORKER_ERROR = (
 )
 
 
-def prepare_database(db_conn, database_engine, config, databases=["main", "state"]):
+def prepare_database(
+    db_conn: Connection,
+    database_engine: BaseDatabaseEngine,
+    config: Optional[HomeServerConfig],
+    databases: Collection[str] = ["main", "state"],
+):
     """Prepares a physical database for usage. Will either create all necessary tables
     or upgrade from an older schema version.
 
@@ -73,16 +81,24 @@ def prepare_database(db_conn, database_engine, config, databases=["main", "state
     Args:
         db_conn:
         database_engine:
-        config (synapse.config.homeserver.HomeServerConfig|None):
+        config :
             application config, or None if we are connecting to an existing
             database which we expect to be configured already
-        databases (list[str]): The name of the databases that will be used
+        databases: The name of the databases that will be used
             with this physical database. Defaults to all databases.
     """
 
     try:
         cur = db_conn.cursor()
 
+        # sqlite does not automatically start transactions for DDL / SELECT statements,
+        # so we start one before running anything. This ensures that any upgrades
+        # are either applied completely, or not at all.
+        #
+        # (psycopg2 automatically starts a transaction as soon as we run any statements
+        # at all, so this is redundant but harmless there.)
+        cur.execute("BEGIN TRANSACTION")
+
         logger.info("%r: Checking existing schema version", databases)
         version_info = _get_or_create_schema_state(cur, database_engine)
 
diff --git a/synapse/storage/util/id_generators.py b/synapse/storage/util/id_generators.py
index b7eb4f8ac9..2a66b3ad4e 100644
--- a/synapse/storage/util/id_generators.py
+++ b/synapse/storage/util/id_generators.py
@@ -224,6 +224,10 @@ class MultiWriterIdGenerator:
         # should be less than the minimum of this set (if not empty).
         self._unfinished_ids = set()  # type: Set[int]
 
+        # Set of local IDs that we've processed that are larger than the current
+        # position, due to there being smaller unpersisted IDs.
+        self._finished_ids = set()  # type: Set[int]
+
         # We track the max position where we know everything before has been
         # persisted. This is done by a) looking at the min across all instances
         # and b) noting that if we have seen a run of persisted positions
@@ -348,17 +352,44 @@ class MultiWriterIdGenerator:
 
     def _mark_id_as_finished(self, next_id: int):
         """The ID has finished being processed so we should advance the
-        current poistion if possible.
+        current position if possible.
         """
 
         with self._lock:
             self._unfinished_ids.discard(next_id)
+            self._finished_ids.add(next_id)
+
+            new_cur = None
+
+            if self._unfinished_ids:
+                # If there are unfinished IDs then the new position will be the
+                # largest finished ID less than the minimum unfinished ID.
+
+                finished = set()
+
+                min_unfinshed = min(self._unfinished_ids)
+                for s in self._finished_ids:
+                    if s < min_unfinshed:
+                        if new_cur is None or new_cur < s:
+                            new_cur = s
+                    else:
+                        finished.add(s)
+
+                # We clear these out since they're now all less than the new
+                # position.
+                self._finished_ids = finished
+            else:
+                # There are no unfinished IDs so the new position is simply the
+                # largest finished one.
+                new_cur = max(self._finished_ids)
+
+                # We clear these out since they're now all less than the new
+                # position.
+                self._finished_ids.clear()
 
-            # Figure out if its safe to advance the position by checking there
-            # aren't any lower allocated IDs that are yet to finish.
-            if all(c > next_id for c in self._unfinished_ids):
+            if new_cur:
                 curr = self._current_positions.get(self._instance_name, 0)
-                self._current_positions[self._instance_name] = max(curr, next_id)
+                self._current_positions[self._instance_name] = max(curr, new_cur)
 
             self._add_persisted_position(next_id)
 
@@ -428,7 +459,7 @@ class MultiWriterIdGenerator:
         # We move the current min position up if the minimum current positions
         # of all instances is higher (since by definition all positions less
         # that that have been persisted).
-        min_curr = min(self._current_positions.values())
+        min_curr = min(self._current_positions.values(), default=0)
         self._persisted_upto_position = max(min_curr, self._persisted_upto_position)
 
         # We now iterate through the seen positions, discarding those that are