diff --git a/src/Discord.Net/DiscordWebSocket.cs b/src/Discord.Net/DiscordWebSocket.cs
index 7d68ea742..0325c659a 100644
--- a/src/Discord.Net/DiscordWebSocket.cs
+++ b/src/Discord.Net/DiscordWebSocket.cs
@@ -15,51 +15,59 @@ namespace Discord
 	{
 		private const int ReceiveChunkSize = 4096;
 		private const int SendChunkSize = 4096;
-		private const int ReadyTimeout = 5000; //Max time in milliseconds between connecting to Discord and receiving a READY event
+		private const int ReadyTimeout = 2500; //Max time in milliseconds between connecting to Discord and receiving a READY event
 
 		private volatile ClientWebSocket _webSocket;
-		private volatile CancellationTokenSource _cancelToken;
+		private volatile CancellationTokenSource _disconnectToken;
 		private volatile Task _tasks;
 		private ConcurrentQueue<byte[]> _sendQueue;
 		private int _heartbeatInterval;
 		private DateTime _lastHeartbeat;
-		private AutoResetEvent _connectWaitOnLogin, _connectWaitOnLogin2;
+		private ManualResetEventSlim _connectWaitOnLogin, _connectWaitOnLogin2;
 		private bool _isConnected;
 
+		public DiscordWebSocket()
+		{
+			_connectWaitOnLogin = new ManualResetEventSlim(false);
+			_connectWaitOnLogin2 = new ManualResetEventSlim(false);
+			
+			_sendQueue = new ConcurrentQueue<byte[]>();
+		}
+
 		public async Task ConnectAsync(string url, bool autoLogin)
 		{
 			await DisconnectAsync();
 
-			_connectWaitOnLogin = new AutoResetEvent(false);
-			_connectWaitOnLogin2 = new AutoResetEvent(false);
-			_sendQueue = new ConcurrentQueue<byte[]>();
+			_disconnectToken = new CancellationTokenSource();
+			var cancelToken = _disconnectToken.Token;
 
 			_webSocket = new ClientWebSocket();
 			_webSocket.Options.KeepAliveInterval = TimeSpan.Zero;
-
-			_cancelToken = new CancellationTokenSource();
-			var cancelToken = _cancelToken.Token;
-
 			await _webSocket.ConnectAsync(new Uri(url), cancelToken);
+
 			_tasks = Task.WhenAll(
 				await Task.Factory.StartNew(ReceiveAsync, cancelToken, TaskCreationOptions.LongRunning, TaskScheduler.Default),
-				await Task.Factory.StartNew(SendAsync, cancelToken, TaskCreationOptions.LongRunning, TaskScheduler.Default)
-			).ContinueWith(x =>
+				await Task.Factory.StartNew(SendAsync, cancelToken, TaskCreationOptions.LongRunning, TaskScheduler.Default))
+			.ContinueWith(x =>
 			{
 				//Do not clean up until both tasks have ended
 				_heartbeatInterval = 0;
 				_lastHeartbeat = DateTime.MinValue;
 				_webSocket.Dispose();
 				_webSocket = null;
-				_cancelToken.Dispose();
-				_cancelToken = null;
+				_disconnectToken.Dispose();
+				_disconnectToken = null;
 				_tasks = null;
 
+				//Clear send queue
+				byte[] ignored;
+				while (_sendQueue.TryDequeue(out ignored)) { }
+
 				if (_isConnected)
 				{
 					_isConnected = false;
 					RaiseDisconnected();
-                }
+				}
 			});
 
 			if (autoLogin)
@@ -67,6 +75,11 @@ namespace Discord
         }
 		public void Login()
 		{
+			var cancelToken = _disconnectToken.Token;
+
+			_connectWaitOnLogin.Reset();
+			_connectWaitOnLogin2.Reset();
+
 			WebSocketCommands.Login msg = new WebSocketCommands.Login();
 			msg.Payload.Token = Http.Token;
 			msg.Payload.Properties["$os"] = "";
@@ -74,11 +87,18 @@ namespace Discord
 			msg.Payload.Properties["$device"] = "Discord.Net";
 			msg.Payload.Properties["$referrer"] = "";
 			msg.Payload.Properties["$referring_domain"] = "";
-			SendMessage(msg, _cancelToken.Token);
+			SendMessage(msg, _disconnectToken.Token);
 
-			if (!_connectWaitOnLogin.WaitOne(ReadyTimeout)) //Pre-Event
-				throw new Exception("No reply from Discord server");
-			_connectWaitOnLogin2.WaitOne(); //Post-Event
+			try
+			{
+				if (!_connectWaitOnLogin.Wait(ReadyTimeout, cancelToken)) //Waiting on READY message
+					throw new Exception("No reply from Discord server");
+			}
+			catch (OperationCanceledException)
+			{
+				throw new InvalidOperationException("Bad Token");
+			}
+			_connectWaitOnLogin2.Wait(cancelToken); //Waiting on READY handler
 
 			_isConnected = true;
 			RaiseConnected();
@@ -87,14 +107,14 @@ namespace Discord
 		{
 			if (_tasks != null)
 			{
-				_cancelToken.Cancel();
+				_disconnectToken.Cancel();
 				await _tasks;
 			}
 		}
 
 		private async Task ReceiveAsync()
 		{
-			var cancelToken = _cancelToken.Token;
+			var cancelToken = _disconnectToken.Token;
 			var buffer = new byte[ReceiveChunkSize];
 			var builder = new StringBuilder();
 
@@ -105,7 +125,7 @@ namespace Discord
 					WebSocketReceiveResult result;
 					do
 					{
-						result = await _webSocket.ReceiveAsync(new ArraySegment<byte>(buffer), _cancelToken.Token);
+						result = await _webSocket.ReceiveAsync(new ArraySegment<byte>(buffer), _disconnectToken.Token);
 
 						if (result.MessageType == WebSocketMessageType.Close)
 						{
@@ -126,8 +146,8 @@ namespace Discord
 							{
 								var payload = (msg.Payload as JToken).ToObject<WebSocketEvents.Ready>();
 								_heartbeatInterval = payload.HeartbeatInterval;
-								SendMessage(new WebSocketCommands.UpdateStatus(), cancelToken);
-								SendMessage(new WebSocketCommands.KeepAlive(), cancelToken);
+								QueueMessage(new WebSocketCommands.UpdateStatus());
+								QueueMessage(new WebSocketCommands.KeepAlive());
 								_connectWaitOnLogin.Set(); //Pre-Event
                             }
 							RaiseGotEvent(msg.Type, msg.Payload as JToken);
@@ -143,12 +163,12 @@ namespace Discord
 				}
 			}
 			catch { }
-			finally { _cancelToken.Cancel(); }
+			finally { _disconnectToken.Cancel(); }
 		}
 
 		private async Task SendAsync()
 		{
-			var cancelToken = _cancelToken.Token;
+			var cancelToken = _disconnectToken.Token;
             try
 			{
 				byte[] bytes;
@@ -159,41 +179,46 @@ namespace Discord
 						DateTime now = DateTime.UtcNow;
 						if ((now - _lastHeartbeat).TotalMilliseconds > _heartbeatInterval)
 						{
-							SendMessage(new WebSocketCommands.KeepAlive(), cancelToken);
+							await SendMessage(new WebSocketCommands.KeepAlive(), cancelToken);
 							_lastHeartbeat = now;
 						}
 					}
 					while (_sendQueue.TryDequeue(out bytes))
-					{
-						var frameCount = (int)Math.Ceiling((double)bytes.Length / SendChunkSize);
-
-						int offset = 0;
-						for (var i = 0; i < frameCount; i++, offset += SendChunkSize)
-						{
-							bool isLast = i == (frameCount - 1);
-
-							int count;
-							if (isLast)
-								count = bytes.Length - (i * SendChunkSize);
-							else
-								count = SendChunkSize;
-
-							await _webSocket.SendAsync(new ArraySegment<byte>(bytes, offset, count), WebSocketMessageType.Text, isLast, cancelToken);
-						}
-					}
+						await SendMessage(bytes, cancelToken);
 					await Task.Delay(100);
 				}
 			}
 			catch { }
-			finally { _cancelToken.Cancel(); }
+			finally { _disconnectToken.Cancel(); }
 		}
 
-		private void SendMessage(object frame, CancellationToken token)
+		private void QueueMessage(object message)
 		{
-			var bytes = Encoding.UTF8.GetBytes(JsonConvert.SerializeObject(frame));
+			var bytes = Encoding.UTF8.GetBytes(JsonConvert.SerializeObject(message));
 			_sendQueue.Enqueue(bytes);
 		}
 
+		private Task SendMessage(object message, CancellationToken cancelToken)
+			=> SendMessage(Encoding.UTF8.GetBytes(JsonConvert.SerializeObject(message)), cancelToken);
+		private async Task SendMessage(byte[] message, CancellationToken cancelToken)
+		{
+			var frameCount = (int)Math.Ceiling((double)message.Length / SendChunkSize);
+
+			int offset = 0;
+			for (var i = 0; i < frameCount; i++, offset += SendChunkSize)
+			{
+				bool isLast = i == (frameCount - 1);
+
+				int count;
+				if (isLast)
+					count = message.Length - (i * SendChunkSize);
+				else
+					count = SendChunkSize;
+
+				await _webSocket.SendAsync(new ArraySegment<byte>(message, offset, count), WebSocketMessageType.Text, isLast, cancelToken);
+			}
+		}
+
 		#region IDisposable Support
 		private bool _isDisposed = false;