diff --git a/src/main/java/org/whispersystems/textsecuregcm/entities/EncryptedOutgoingMessage.java b/src/main/java/org/whispersystems/textsecuregcm/entities/EncryptedOutgoingMessage.java
index d286ac578..32a90a504 100644
--- a/src/main/java/org/whispersystems/textsecuregcm/entities/EncryptedOutgoingMessage.java
+++ b/src/main/java/org/whispersystems/textsecuregcm/entities/EncryptedOutgoingMessage.java
@@ -1,4 +1,4 @@
-/**
+/*
  * Copyright (C) 2013 Open WhisperSystems
  *
  * This program is free software: you can redistribute it and/or modify
@@ -42,21 +42,15 @@ public class EncryptedOutgoingMessage {
   private static final int    MAC_SIZE        = 10;
 
   private final byte[] serialized;
-  private final String serializedAndEncoded;
 
   public EncryptedOutgoingMessage(Envelope outgoingMessage, String signalingKey)
       throws CryptoEncodingException
   {
-    byte[]        plaintext  = outgoingMessage.toByteArray();
-    SecretKeySpec cipherKey  = getCipherKey (signalingKey);
-    SecretKeySpec macKey     = getMacKey(signalingKey);
+    byte[]        plaintext = outgoingMessage.toByteArray();
+    SecretKeySpec cipherKey = getCipherKey (signalingKey);
+    SecretKeySpec macKey    = getMacKey(signalingKey);
 
-    this.serialized           = getCiphertext(plaintext, cipherKey, macKey);
-    this.serializedAndEncoded = Base64.encodeBytes(this.serialized);
-  }
-
-  public String toEncodedString() {
-    return serializedAndEncoded;
+    this.serialized         = getCiphertext(plaintext, cipherKey, macKey);
   }
 
   public byte[] toByteArray() {
diff --git a/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java b/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
index b6d9465b6..24df71ac9 100644
--- a/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
+++ b/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
@@ -31,6 +31,7 @@ import org.whispersystems.websocket.messages.WebSocketResponseMessage;
 import javax.annotation.Nonnull;
 import javax.annotation.Nullable;
 import javax.ws.rs.WebApplicationException;
+import java.util.Collections;
 import java.util.Iterator;
 import java.util.Optional;
 
@@ -111,9 +112,18 @@ public class WebSocketConnection implements DispatchChannel {
                            final boolean                     requery)
   {
     try {
-      EncryptedOutgoingMessage                   encryptedMessage = new EncryptedOutgoingMessage(message, device.getSignalingKey());
-      Optional<byte[]>                           body             = Optional.ofNullable(encryptedMessage.toByteArray());
-      ListenableFuture<WebSocketResponseMessage> response         = client.sendRequest("PUT", "/api/v1/message", null, body);
+      String           header;
+      Optional<byte[]> body;
+
+      if (Util.isEmpty(device.getSignalingKey())) {
+        header = "X-Signal-Key: false";
+        body   = Optional.ofNullable(message.toByteArray());
+      } else {
+        header = "X-Signal-Key: true";
+        body   = Optional.ofNullable(new EncryptedOutgoingMessage(message, device.getSignalingKey()).toByteArray());
+      }
+
+      ListenableFuture<WebSocketResponseMessage> response = client.sendRequest("PUT", "/api/v1/message", Collections.singletonList(header), body);
 
       Futures.addCallback(response, new FutureCallback<WebSocketResponseMessage>() {
         @Override