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 6d9f8779e..fded9d827 100644
--- a/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
+++ b/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
@@ -219,39 +219,35 @@ public class WebSocketConnection implements DisconnectionRequestListener {
               .thenReturn(entry);
           case MessageStreamEntry.QueueEmpty _ -> Mono.just(entry);
         }, MESSAGE_SENDER_MAX_CONCURRENCY)
-        .subscribeOn(messageDeliveryScheduler)
-        .subscribe(
-            entry -> {
-              if (entry instanceof MessageStreamEntry.QueueEmpty) {
-                final Duration drainDuration = Duration.ofNanos(System.nanoTime() - queueDrainStartNanos);
+        // `ConflictingMessageConsumerException` is handled before processing messages
+        .doOnError(throwable -> !(throwable instanceof ConflictingMessageConsumerException), throwable -> {
+          measureSendMessageErrors(throwable);
 
-                Metrics.summary(INITIAL_QUEUE_LENGTH_DISTRIBUTION_NAME, platformTag).record(sentMessageCounter.sum());
-                Metrics.timer(INITIAL_QUEUE_DRAIN_TIMER_NAME, platformTag).record(drainDuration);
+          if (!client.isOpen()) {
+            logger.debug("Client disconnected before queue cleared");
+            return;
+          }
 
-                if (drainDuration.compareTo(SLOW_DRAIN_THRESHOLD) > 0) {
-                  Metrics.counter(SLOW_QUEUE_DRAIN_COUNTER_NAME, platformTag).increment();
-                }
+          client.close(1011, "Failed to retrieve messages");
+        })
+        // Make sure we process message acknowledgements before sending the "queue clear" signal
+        .doOnNext(entry -> {
+          if (entry instanceof MessageStreamEntry.QueueEmpty) {
+            final Duration drainDuration = Duration.ofNanos(System.nanoTime() - queueDrainStartNanos);
 
-                client.sendRequest("PUT", "/api/v1/queue/empty",
-                    Collections.singletonList(HeaderUtils.getTimestampHeader()), Optional.empty());
-              }
-            },
-            throwable -> {
-              // `ConflictingMessageConsumerException` is handled before processing messages
-              if (throwable instanceof ConflictingMessageConsumerException) {
-                return;
-              }
+            Metrics.summary(INITIAL_QUEUE_LENGTH_DISTRIBUTION_NAME, platformTag).record(sentMessageCounter.sum());
+            Metrics.timer(INITIAL_QUEUE_DRAIN_TIMER_NAME, platformTag).record(drainDuration);
 
-              measureSendMessageErrors(throwable);
-
-              if (!client.isOpen()) {
-                logger.debug("Client disconnected before queue cleared");
-                return;
-              }
-
-              client.close(1011, "Failed to retrieve messages");
+            if (drainDuration.compareTo(SLOW_DRAIN_THRESHOLD) > 0) {
+              Metrics.counter(SLOW_QUEUE_DRAIN_COUNTER_NAME, platformTag).increment();
             }
-        ));
+
+            client.sendRequest("PUT", "/api/v1/queue/empty",
+                Collections.singletonList(HeaderUtils.getTimestampHeader()), Optional.empty());
+          }
+        })
+        .subscribeOn(messageDeliveryScheduler)
+        .subscribe());
   }
 
   public void stop() {