diff --git a/synapse/handlers/delayed_events.py b/synapse/handlers/delayed_events.py
index caabce8e4ce..fc9baaf6943 100644
--- a/synapse/handlers/delayed_events.py
+++ b/synapse/handlers/delayed_events.py
@@ -30,13 +30,11 @@
 )
 
 import attr
-from twisted.internet import defer
 from twisted.internet.interfaces import IDelayedCall
 
 from synapse.api.constants import EventTypes
 from synapse.api.errors import Codes, NotFoundError, ShadowBanError, SynapseError
 from synapse.events import EventBase
-from synapse.logging.context import make_deferred_yieldable
 from synapse.logging.opentracing import set_tag
 from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.databases.main.delayed_events import (
@@ -92,15 +90,8 @@ def __init__(self, hs: "HomeServer"):
         async def _schedule_db_events() -> None:
             # TODO: Sync all state first, so that affected delayed state events will be cancelled
             events, remaining_timeout_delays = await self.store.process_all_delays(self._get_current_ts())
-            await make_deferred_yieldable(
-                defer.gatherResults(
-                    [
-                        run_as_background_process("_send_event", self._send_event, *args)
-                        for args in events
-                    ],
-                    consumeErrors=True,
-                )
-            )
+            for args in events:
+                await self._send_event(*args)
 
             for delay_id, user_localpart, relative_delay in remaining_timeout_delays:
                 self._schedule(delay_id, user_localpart, relative_delay)
@@ -243,14 +234,11 @@ async def update(self, requester: Requester, delay_id: str, action: str) -> None
                 self._schedule(delay_id, user_localpart, delay)
 
             elif enum_action == _UpdateDelayedEventAction.SEND:
-                await self._send_now(delay_id, user_localpart)
-
-    async def _send_now(self, delay_id: DelayID, user_localpart: UserLocalpart) -> None:
-        args, removed_timeout_delay_ids = await self.store.pop_event(delay_id, user_localpart)
+                args, removed_timeout_delay_ids = await self.store.pop_event(delay_id, user_localpart)
 
-        for timeout_delay_id in removed_timeout_delay_ids:
-            self._unschedule(timeout_delay_id, user_localpart)
-        await self._send_event(user_localpart, *args)
+                for timeout_delay_id in removed_timeout_delay_ids:
+                    self._unschedule(timeout_delay_id, user_localpart)
+                await self._send_event(user_localpart, *args)
 
     async def _send_on_timeout(self, delay_id: DelayID, user_localpart: UserLocalpart) -> None:
         del self._delayed_calls[_DelayedCallKey(delay_id, user_localpart)]
diff --git a/synapse/storage/databases/main/delayed_events.py b/synapse/storage/databases/main/delayed_events.py
index ef4921d77ab..bd876b36e9d 100644
--- a/synapse/storage/databases/main/delayed_events.py
+++ b/synapse/storage/databases/main/delayed_events.py
@@ -61,6 +61,16 @@
     JsonDict,
 ]
 
+# TODO: If a Tuple type hint can be extended, extend the above one
+DelayedPartialEventWithUser = Tuple[
+    UserLocalpart,
+    RoomID,
+    EventType,
+    Optional[StateKey],
+    Optional[Timestamp],
+    JsonDict,
+]
+
 
 # TODO: Try to support workers
 class DelayedEventsStore(SQLBaseStore):
@@ -295,7 +305,7 @@ async def get_all_for_user(
         ]
 
     async def process_all_delays(self, current_ts: Timestamp) -> Tuple[
-        List[DelayedPartialEvent],
+        List[DelayedPartialEventWithUser],
         List[Tuple[DelayID, UserLocalpart, Delay]],
     ]:
         """
@@ -305,34 +315,34 @@ async def process_all_delays(self, current_ts: Timestamp) -> Tuple[
         """
 
         def process_all_delays_txn(txn: LoggingTransaction) -> Tuple[
-            List[DelayedPartialEvent],
+            List[DelayedPartialEventWithUser],
             List[Tuple[DelayID, UserLocalpart, Delay]],
         ]:
-            events: List[DelayedPartialEvent] = []
+            events: List[DelayedPartialEventWithUser] = []
             removed_timeout_delay_ids: Set[DelayID] = set()
 
             txn.execute(
                 """
                 WITH delay_send_times AS (
-                    SELECT delay_rowid, running_since + delay AS send_ts
+                    SELECT delay_rowid, user_localpart, running_since + delay AS send_ts
                     FROM delayed_events JOIN delayed_event_timeouts USING (delay_rowid)
                 )
-                SELECT delay_rowid
+                SELECT delay_rowid, user_localpart
                 FROM delay_send_times
                 WHERE send_ts < ?
                 ORDER BY send_ts
                 """,
                 (current_ts,),
             )
-            for (delay_rowid,) in txn:
+            for row in txn:
                 try:
                     event, removed_timeout_delay_id = self._pop_event_txn(
                         txn,
-                        keyvalues={"delay_rowid": delay_rowid},
+                        keyvalues={"delay_rowid": row[0]},
                     )
                 except NotFoundError:
                     pass
-                events.append(event)
+                events.append((UserLocalpart(row[1]), *event))
                 removed_timeout_delay_ids |= removed_timeout_delay_id
 
             txn.execute(