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 d23cc8a88..dda6b2d56 100644
--- a/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
+++ b/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
@@ -126,7 +126,7 @@ public class WebSocketConnection implements DispatchChannel, MessageAvailability
     processStoredMessages();
   }
 
-  private CompletableFuture<Void> sendMessage(final Envelope message, final Optional<StoredMessageInfo> storedMessageInfo) {
+  private CompletableFuture<WebSocketResponseMessage> sendMessage(final Envelope message, final Optional<StoredMessageInfo> storedMessageInfo) {
     try {
       String           header;
       Optional<byte[]> body;
@@ -141,25 +141,24 @@ public class WebSocketConnection implements DispatchChannel, MessageAvailability
 
       sendMessageMeter.mark();
 
-      return client.sendRequest("PUT", "/api/v1/message", List.of(header, TimestampHeaderUtil.getTimestampHeader()), body)
-            .thenAccept(response -> {
-              boolean isReceipt = message.getType() == Envelope.Type.RECEIPT;
+      return client.sendRequest("PUT", "/api/v1/message", List.of(header, TimestampHeaderUtil.getTimestampHeader()), body).whenComplete((response, throwable) -> {
+        if (throwable == null) {
+          boolean isReceipt = message.getType() == Envelope.Type.RECEIPT;
 
-              if (isSuccessResponse(response) && !isReceipt) {
-                messageTime.update(System.currentTimeMillis() - message.getTimestamp());
-              }
+          if (isSuccessResponse(response) && !isReceipt) {
+            messageTime.update(System.currentTimeMillis() - message.getTimestamp());
+          }
 
-              if (isSuccessResponse(response)) {
-                if (storedMessageInfo.isPresent()) messagesManager.delete(account.getNumber(), account.getUuid(), device.getId(), storedMessageInfo.get().id, storedMessageInfo.get().cached);
-                if (!isReceipt)                    sendDeliveryReceiptFor(message);
-              } else if (!isSuccessResponse(response) && !storedMessageInfo.isPresent()) {
-                requeueMessage(message);
-              }
-            })
-            .exceptionally(throwable ->  {
-              if (!storedMessageInfo.isPresent()) requeueMessage(message);
-              return null;
-            });
+          if (isSuccessResponse(response)) {
+            if (storedMessageInfo.isPresent()) messagesManager.delete(account.getNumber(), account.getUuid(), device.getId(), storedMessageInfo.get().id, storedMessageInfo.get().cached);
+            if (!isReceipt)                    sendDeliveryReceiptFor(message);
+          } else if (!isSuccessResponse(response) && !storedMessageInfo.isPresent()) {
+            requeueMessage(message);
+          }
+        } else {
+          if (!storedMessageInfo.isPresent()) requeueMessage(message);
+        }
+      });
     } catch (CryptoEncodingException e) {
       logger.warn("Bad signaling key", e);
       return CompletableFuture.failedFuture(e);
@@ -201,13 +200,13 @@ public class WebSocketConnection implements DispatchChannel, MessageAvailability
       sendNextMessagePage(state != StoredMessageState.PERSISTED_NEW_MESSAGES_AVAILABLE, queueClearedFuture);
 
       queueClearedFuture.whenComplete((v, cause) -> {
-        if (sentInitialQueueEmptyMessage.compareAndSet(false, true)) {
+        if (cause == null && sentInitialQueueEmptyMessage.compareAndSet(false, true)) {
           client.sendRequest("PUT", "/api/v1/queue/empty", Collections.singletonList(TimestampHeaderUtil.getTimestampHeader()), Optional.empty());
         }
 
         processStoredMessagesSemaphore.release();
 
-        if (storedMessageState.get() != StoredMessageState.EMPTY) {
+        if (cause == null && storedMessageState.get() != StoredMessageState.EMPTY) {
           processStoredMessages();
         }
       });
@@ -227,7 +226,7 @@ public class WebSocketConnection implements DispatchChannel, MessageAvailability
 
       if (!Util.isEmpty(message.getSource())) {
         builder.setSource(message.getSource())
-                .setSourceDevice(message.getSourceDevice());
+               .setSourceDevice(message.getSourceDevice());
       }
 
       if (message.getMessage() != null) {
@@ -246,10 +245,14 @@ public class WebSocketConnection implements DispatchChannel, MessageAvailability
     }
 
     CompletableFuture.allOf(sendFutures).whenComplete((v, cause) -> {
-      if (messages.hasMore()) {
-        sendNextMessagePage(cachedMessagesOnly, queueClearedFuture);
+      if (cause == null) {
+        if (messages.hasMore()) {
+          sendNextMessagePage(cachedMessagesOnly, queueClearedFuture);
+        } else {
+          queueClearedFuture.complete(null);
+        }
       } else {
-        queueClearedFuture.complete(null);
+        queueClearedFuture.completeExceptionally(cause);
       }
     });
   }