diff --git a/federationapi/queue/destinationqueue.go b/federationapi/queue/destinationqueue.go
index 1b7670e9..a638a574 100644
--- a/federationapi/queue/destinationqueue.go
+++ b/federationapi/queue/destinationqueue.go
@@ -76,21 +76,25 @@ func (oq *destinationQueue) sendEvent(event *gomatrixserverlib.HeaderedEvent, re
 		return
 	}
 
-	// If there's room in memory to hold the event then add it to the
-	// list.
-	oq.pendingMutex.Lock()
-	if len(oq.pendingPDUs) < maxPDUsInMemory {
-		oq.pendingPDUs = append(oq.pendingPDUs, &queuedPDU{
-			pdu:     event,
-			receipt: receipt,
-		})
-	} else {
-		oq.overflowed.Store(true)
-	}
-	oq.pendingMutex.Unlock()
+	// Check if the destination is blacklisted. If it isn't then wake
+	// up the queue.
+	if !oq.statistics.Blacklisted() {
+		// If there's room in memory to hold the event then add it to the
+		// list.
+		oq.pendingMutex.Lock()
+		if len(oq.pendingPDUs) < maxPDUsInMemory {
+			oq.pendingPDUs = append(oq.pendingPDUs, &queuedPDU{
+				pdu:     event,
+				receipt: receipt,
+			})
+		} else {
+			oq.overflowed.Store(true)
+		}
+		oq.pendingMutex.Unlock()
 
-	if !oq.backingOff.Load() {
-		oq.wakeQueueAndNotify()
+		if !oq.backingOff.Load() {
+			oq.wakeQueueAndNotify()
+		}
 	}
 }
 
@@ -103,21 +107,25 @@ func (oq *destinationQueue) sendEDU(event *gomatrixserverlib.EDU, receipt *share
 		return
 	}
 
-	// If there's room in memory to hold the event then add it to the
-	// list.
-	oq.pendingMutex.Lock()
-	if len(oq.pendingEDUs) < maxEDUsInMemory {
-		oq.pendingEDUs = append(oq.pendingEDUs, &queuedEDU{
-			edu:     event,
-			receipt: receipt,
-		})
-	} else {
-		oq.overflowed.Store(true)
-	}
-	oq.pendingMutex.Unlock()
+	// Check if the destination is blacklisted. If it isn't then wake
+	// up the queue.
+	if !oq.statistics.Blacklisted() {
+		// If there's room in memory to hold the event then add it to the
+		// list.
+		oq.pendingMutex.Lock()
+		if len(oq.pendingEDUs) < maxEDUsInMemory {
+			oq.pendingEDUs = append(oq.pendingEDUs, &queuedEDU{
+				edu:     event,
+				receipt: receipt,
+			})
+		} else {
+			oq.overflowed.Store(true)
+		}
+		oq.pendingMutex.Unlock()
 
-	if !oq.backingOff.Load() {
-		oq.wakeQueueAndNotify()
+		if !oq.backingOff.Load() {
+			oq.wakeQueueAndNotify()
+		}
 	}
 }
 
diff --git a/federationapi/queue/queue.go b/federationapi/queue/queue.go
index 32833437..b5d0552c 100644
--- a/federationapi/queue/queue.go
+++ b/federationapi/queue/queue.go
@@ -247,9 +247,10 @@ func (oqs *OutgoingQueues) SendEvent(
 		return fmt.Errorf("sendevent: oqs.db.StoreJSON: %w", err)
 	}
 
+	destQueues := make([]*destinationQueue, 0, len(destmap))
 	for destination := range destmap {
-		if queue := oqs.getQueue(destination); queue != nil && !queue.statistics.Blacklisted() {
-			queue.sendEvent(ev, nid)
+		if queue := oqs.getQueue(destination); queue != nil {
+			destQueues = append(destQueues, queue)
 		} else {
 			delete(destmap, destination)
 		}
@@ -267,6 +268,14 @@ func (oqs *OutgoingQueues) SendEvent(
 		return err
 	}
 
+	// NOTE : PDUs should be associated with destinations before sending
+	// them, otherwise this is technically a race.
+	// If the send completes before they are associated then they won't
+	// get properly cleaned up in the database.
+	for _, queue := range destQueues {
+		queue.sendEvent(ev, nid)
+	}
+
 	return nil
 }
 
@@ -335,20 +344,21 @@ func (oqs *OutgoingQueues) SendEDU(
 		return fmt.Errorf("sendevent: oqs.db.StoreJSON: %w", err)
 	}
 
+	destQueues := make([]*destinationQueue, 0, len(destmap))
 	for destination := range destmap {
-		if queue := oqs.getQueue(destination); queue != nil && !queue.statistics.Blacklisted() {
-			queue.sendEDU(e, nid)
+		if queue := oqs.getQueue(destination); queue != nil {
+			destQueues = append(destQueues, queue)
 		} else {
 			delete(destmap, destination)
 		}
 	}
 
 	// Create a database entry that associates the given PDU NID with
-	// this destination queue. We'll then be able to retrieve the PDU
+	// these destination queues. We'll then be able to retrieve the PDU
 	// later.
 	if err := oqs.db.AssociateEDUWithDestinations(
 		oqs.process.Context(),
-		destmap, // the destination server name
+		destmap, // the destination server names
 		nid,     // NIDs from federationapi_queue_json table
 		e.Type,
 		nil, // this will use the default expireEDUTypes map
@@ -357,6 +367,14 @@ func (oqs *OutgoingQueues) SendEDU(
 		return err
 	}
 
+	// NOTE : EDUs should be associated with destinations before sending
+	// them, otherwise this is technically a race.
+	// If the send completes before they are associated then they won't
+	// get properly cleaned up in the database.
+	for _, queue := range destQueues {
+		queue.sendEDU(e, nid)
+	}
+
 	return nil
 }