diff --git a/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java b/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
index a715def60..d23cc8a88 100644
--- a/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
+++ b/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
@@ -195,17 +195,26 @@ public class WebSocketConnection implements DispatchChannel, MessageAvailability
   @VisibleForTesting
   void processStoredMessages() {
     if (processStoredMessagesSemaphore.tryAcquire()) {
-      final StoredMessageState state = storedMessageState.getAndSet(StoredMessageState.EMPTY);
+      final StoredMessageState      state              = storedMessageState.getAndSet(StoredMessageState.EMPTY);
+      final CompletableFuture<Void> queueClearedFuture = new CompletableFuture<>();
+
+      sendNextMessagePage(state != StoredMessageState.PERSISTED_NEW_MESSAGES_AVAILABLE, queueClearedFuture);
+
+      queueClearedFuture.whenComplete((v, cause) -> {
+        if (sentInitialQueueEmptyMessage.compareAndSet(false, true)) {
+          client.sendRequest("PUT", "/api/v1/queue/empty", Collections.singletonList(TimestampHeaderUtil.getTimestampHeader()), Optional.empty());
+        }
 
-      if (state == StoredMessageState.CACHED_NEW_MESSAGES_AVAILABLE || state == StoredMessageState.PERSISTED_NEW_MESSAGES_AVAILABLE) {
-        sendNextMessagePage(state == StoredMessageState.CACHED_NEW_MESSAGES_AVAILABLE);
-      } else {
         processStoredMessagesSemaphore.release();
-      }
+
+        if (storedMessageState.get() != StoredMessageState.EMPTY) {
+          processStoredMessages();
+        }
+      });
     }
   }
 
-  private void sendNextMessagePage(final boolean cachedMessagesOnly) {
+  private void sendNextMessagePage(final boolean cachedMessagesOnly, final CompletableFuture<Void> queueClearedFuture) {
     final OutgoingMessageEntityList messages    = messagesManager.getMessagesForDevice(account.getNumber(), account.getUuid(), device.getId(), client.getUserAgent(), cachedMessagesOnly);
     final CompletableFuture<?>[]    sendFutures = new CompletableFuture[messages.getMessages().size()];
 
@@ -238,14 +247,9 @@ public class WebSocketConnection implements DispatchChannel, MessageAvailability
 
     CompletableFuture.allOf(sendFutures).whenComplete((v, cause) -> {
       if (messages.hasMore()) {
-        sendNextMessagePage(cachedMessagesOnly);
+        sendNextMessagePage(cachedMessagesOnly, queueClearedFuture);
       } else {
-        if (sentInitialQueueEmptyMessage.compareAndSet(false, true)) {
-          client.sendRequest("PUT", "/api/v1/queue/empty", Collections.singletonList(TimestampHeaderUtil.getTimestampHeader()), Optional.empty());
-        }
-
-        processStoredMessagesSemaphore.release();
-        processStoredMessages();
+        queueClearedFuture.complete(null);
       }
     });
   }