diff --git a/keyserver/internal/device_list_update.go b/keyserver/internal/device_list_update.go
index 85785b07c..1c4f0b970 100644
--- a/keyserver/internal/device_list_update.go
+++ b/keyserver/internal/device_list_update.go
@@ -67,6 +67,11 @@ type DeviceListUpdater struct {
 	producer    KeyChangeProducer
 	fedClient   *gomatrixserverlib.FederationClient
 	workerChans []chan gomatrixserverlib.ServerName
+
+	// When device lists are stale for a user, they get inserted into this map with a channel which `Update` will
+	// block on or timeout via a select.
+	userIDToChan   map[string]chan bool
+	userIDToChanMu *sync.Mutex
 }
 
 // DeviceListUpdaterDatabase is the subset of functionality from storage.Database required for the updater.
@@ -98,12 +103,14 @@ func NewDeviceListUpdater(
 	numWorkers int,
 ) *DeviceListUpdater {
 	return &DeviceListUpdater{
-		userIDToMutex: make(map[string]*sync.Mutex),
-		mu:            &sync.Mutex{},
-		db:            db,
-		producer:      producer,
-		fedClient:     fedClient,
-		workerChans:   make([]chan gomatrixserverlib.ServerName, numWorkers),
+		userIDToMutex:  make(map[string]*sync.Mutex),
+		mu:             &sync.Mutex{},
+		db:             db,
+		producer:       producer,
+		fedClient:      fedClient,
+		workerChans:    make([]chan gomatrixserverlib.ServerName, numWorkers),
+		userIDToChan:   make(map[string]chan bool),
+		userIDToChanMu: &sync.Mutex{},
 	}
 }
 
@@ -137,6 +144,8 @@ func (u *DeviceListUpdater) mutex(userID string) *sync.Mutex {
 	return u.userIDToMutex[userID]
 }
 
+// Update blocks until the update has been stored in the database. It blocks primarily for satisfying sytest,
+// which assumes when /send 200 OKs that the device lists have been updated.
 func (u *DeviceListUpdater) Update(ctx context.Context, event gomatrixserverlib.DeviceListUpdateEvent) error {
 	isDeviceListStale, err := u.update(ctx, event)
 	if err != nil {
@@ -213,7 +222,35 @@ func (u *DeviceListUpdater) notifyWorkers(userID string) {
 	hash := fnv.New32a()
 	_, _ = hash.Write([]byte(remoteServer))
 	index := int(hash.Sum32()) % len(u.workerChans)
+
+	ch := u.assignChannel(userID)
 	u.workerChans[index] <- remoteServer
+	select {
+	case <-ch:
+	case <-time.After(10 * time.Second):
+		// we don't return an error in this case as it's not a failure condition.
+		// we mainly block for the benefit of sytest anyway
+	}
+}
+
+func (u *DeviceListUpdater) assignChannel(userID string) chan bool {
+	u.userIDToChanMu.Lock()
+	defer u.userIDToChanMu.Unlock()
+	if ch, ok := u.userIDToChan[userID]; ok {
+		return ch
+	}
+	ch := make(chan bool)
+	u.userIDToChan[userID] = ch
+	return ch
+}
+
+func (u *DeviceListUpdater) clearChannel(userID string) {
+	u.userIDToChanMu.Lock()
+	defer u.userIDToChanMu.Unlock()
+	if ch, ok := u.userIDToChan[userID]; ok {
+		close(ch)
+		delete(u.userIDToChan, userID)
+	}
 }
 
 func (u *DeviceListUpdater) worker(ch chan gomatrixserverlib.ServerName) {
@@ -285,6 +322,8 @@ func (u *DeviceListUpdater) processServer(serverName gomatrixserverlib.ServerNam
 		if err != nil {
 			logger.WithError(err).WithField("user_id", userID).Error("fetched device list but failed to store/emit it")
 			hasFailures = true
+		} else {
+			u.clearChannel(userID)
 		}
 	}
 	return hasFailures
diff --git a/keyserver/internal/device_list_update_test.go b/keyserver/internal/device_list_update_test.go
index b07148bbd..dcb981c4f 100644
--- a/keyserver/internal/device_list_update_test.go
+++ b/keyserver/internal/device_list_update_test.go
@@ -204,16 +204,6 @@ func TestUpdateNoPrevID(t *testing.T) {
 	if err != nil {
 		t.Fatalf("Update returned an error: %s", err)
 	}
-	// At this point we show have this device list marked as stale and not store the keys or emitted anything
-	if !db.staleUsers[event.UserID] {
-		t.Errorf("%s not marked as stale", event.UserID)
-	}
-	if len(producer.events) > 0 {
-		t.Errorf("Update incorrect emitted %d device change events", len(producer.events))
-	}
-	if len(db.storedKeys) > 0 {
-		t.Errorf("Update incorrect stored %d device change events", len(db.storedKeys))
-	}
 	t.Log("waiting for /users/devices to be called...")
 	wg.Wait()
 	// wait a bit for db to be updated...
diff --git a/sytest-whitelist b/sytest-whitelist
index 4d37b3ee1..bbac69728 100644
--- a/sytest-whitelist
+++ b/sytest-whitelist
@@ -143,6 +143,7 @@ Device deletion propagates over federation
 If remote user leaves room, changes device and rejoins we see update in sync
 If remote user leaves room, changes device and rejoins we see update in /keys/changes
 If remote user leaves room we no longer receive device updates
+If a device list update goes missing, the server resyncs on the next one
 Get left notifs in sync and /keys/changes when other user leaves
 Can query remote device keys using POST after notification
 Can add account data