diff --git a/src/Elasticsearch.Net/Connection/HttpConnection.cs b/src/Elasticsearch.Net/Connection/HttpConnection.cs
index a1e78a7a43f..0b08af9754d 100644
--- a/src/Elasticsearch.Net/Connection/HttpConnection.cs
+++ b/src/Elasticsearch.Net/Connection/HttpConnection.cs
@@ -180,7 +180,7 @@ public virtual ElasticsearchResponse<TReturn> Request<TReturn>(RequestData reque
 		}
 
 
-		private static void RegisterApmTaskTimeout(IAsyncResult result, WebRequest request, RequestData requestData) =>
+		private static RegisteredWaitHandle RegisterApmTaskTimeout(IAsyncResult result, WebRequest request, RequestData requestData) =>
 			ThreadPool.RegisterWaitForSingleObject(result.AsyncWaitHandle, TimeoutCallback, request, requestData.RequestTimeout, true);
 
 		private static void TimeoutCallback(object state, bool timedOut)
@@ -189,69 +189,82 @@ private static void TimeoutCallback(object state, bool timedOut)
 			(state as WebRequest)?.Abort();
 		}
 
-		public virtual async Task<ElasticsearchResponse<TReturn>> RequestAsync<TReturn>(RequestData requestData, CancellationToken cancellationToken) where TReturn : class
+		public virtual async Task<ElasticsearchResponse<TReturn>> RequestAsync<TReturn>(RequestData requestData,
+			CancellationToken cancellationToken) where TReturn : class
 		{
 			var builder = new ResponseBuilder<TReturn>(requestData, cancellationToken);
+			WaitHandle apmWaitHandle = null;
+			RegisteredWaitHandle apmTaskTimeout = null;
 			try
 			{
-				var request = this.CreateHttpWebRequest(requestData);
-				cancellationToken.Register(()=>request.Abort());
 				var data = requestData.PostData;
-
-				if (data != null)
+				var request = this.CreateHttpWebRequest(requestData);
+				using (cancellationToken.Register(() => request.Abort()))
 				{
-					var apmGetRequestStreamTask = Task.Factory.FromAsync(request.BeginGetRequestStream, request.EndGetRequestStream, null);
-					RegisterApmTaskTimeout(apmGetRequestStreamTask, request, requestData);
-
-					using (var stream = await apmGetRequestStreamTask.ConfigureAwait(false))
-					{
-						if (requestData.HttpCompression)
-							using (var zipStream = new GZipStream(stream, CompressionMode.Compress))
-								await data.WriteAsync(zipStream, requestData.ConnectionSettings, cancellationToken).ConfigureAwait(false);
-						else
-							await data.WriteAsync(stream, requestData.ConnectionSettings, cancellationToken).ConfigureAwait(false);
-					}
+					if (data != null)
+						await PostRequestAsync(requestData, cancellationToken, request, data);
+					requestData.MadeItToResponse = true;
+                    //http://msdn.microsoft.com/en-us/library/system.net.httpwebresponse.getresponsestream.aspx
+                    //Either the stream or the response object needs to be closed but not both although it won't
+                    //throw any errors if both are closed atleast one of them has to be Closed.
+                    //Since we expose the stream we let closing the stream determining when to close the connection
+
+                    var apmGetResponseTask = Task.Factory.FromAsync(request.BeginGetResponse, request.EndGetResponse, null);
+                    apmWaitHandle = ((IAsyncResult) apmGetResponseTask).AsyncWaitHandle;
+                    apmTaskTimeout = RegisterApmTaskTimeout(apmGetResponseTask, request, requestData);
+
+                    var response = (HttpWebResponse) (await apmGetResponseTask.ConfigureAwait(false));
+                    builder.StatusCode = (int) response.StatusCode;
+                    builder.Stream = response.GetResponseStream();
+                    if (response.SupportsHeaders && response.Headers.HasKeys() && response.Headers.AllKeys.Contains("Warning"))
+                        builder.DeprecationWarnings = response.Headers.GetValues("Warning");
+                    // https://github.com/elastic/elasticsearch-net/issues/2311
+                    // if stream is null call dispose on response instead.
+                    if (builder.Stream == null || builder.Stream == Stream.Null) response.Dispose();
+                    if (apmWaitHandle != null) apmTaskTimeout?.Unregister(apmWaitHandle);
 				}
-				requestData.MadeItToResponse = true;
-
-				//http://msdn.microsoft.com/en-us/library/system.net.httpwebresponse.getresponsestream.aspx
-				//Either the stream or the response object needs to be closed but not both although it won't
-				//throw any errors if both are closed atleast one of them has to be Closed.
-				//Since we expose the stream we let closing the stream determining when to close the connection
-
-				var apmGetResponseTask = Task.Factory.FromAsync(request.BeginGetResponse, request.EndGetResponse, null);
-				RegisterApmTaskTimeout(apmGetResponseTask, request, requestData);
-
-				var response = (HttpWebResponse)(await apmGetResponseTask.ConfigureAwait(false));
-				builder.StatusCode = (int)response.StatusCode;
-				builder.Stream = response.GetResponseStream();
-				if (response.SupportsHeaders && response.Headers.HasKeys() && response.Headers.AllKeys.Contains("Warning"))
-					builder.DeprecationWarnings = response.Headers.GetValues("Warning");
-				// https://github.com/elastic/elasticsearch-net/issues/2311
-				// if stream is null call dispose on response instead.
-				if (builder.Stream == null || builder.Stream == Stream.Null) response.Dispose();
 			}
 			catch (WebException e)
 			{
+				if (apmWaitHandle != null) apmTaskTimeout?.Unregister(apmWaitHandle);
 				HandleException(builder, e);
 			}
-
+			catch
+			{
+				if (apmWaitHandle != null) apmTaskTimeout?.Unregister(apmWaitHandle);
+				throw;
+			}
 			return await builder.ToResponseAsync().ConfigureAwait(false);
 		}
 
+		private static async Task PostRequestAsync(RequestData requestData, CancellationToken cancellationToken, HttpWebRequest request,
+			PostData<object> data)
+		{
+			var apmGetRequestStreamTask = Task.Factory.FromAsync(request.BeginGetRequestStream, request.EndGetRequestStream, null);
+			var getRequestStreamCancellationHandle = RegisterApmTaskTimeout(apmGetRequestStreamTask, request, requestData);
+
+			using (var stream = await apmGetRequestStreamTask.ConfigureAwait(false))
+			{
+				if (requestData.HttpCompression)
+					using (var zipStream = new GZipStream(stream, CompressionMode.Compress))
+						await data.WriteAsync(zipStream, requestData.ConnectionSettings, cancellationToken).ConfigureAwait(false);
+				else
+					await data.WriteAsync(stream, requestData.ConnectionSettings, cancellationToken).ConfigureAwait(false);
+			}
+			getRequestStreamCancellationHandle.Unregister(((IAsyncResult) apmGetRequestStreamTask).AsyncWaitHandle);
+		}
+
 		private void HandleException<TReturn>(ResponseBuilder<TReturn> builder, WebException exception)
 			where TReturn : class
 		{
 			builder.Exception = exception;
 			var response = exception.Response as HttpWebResponse;
-			if (response != null)
-			{
-				builder.StatusCode = (int)response.StatusCode;
-				builder.Stream = response.GetResponseStream();
-				// https://github.com/elastic/elasticsearch-net/issues/2311
-				// if stream is null call dispose on response instead.
-				if (builder.Stream == null || builder.Stream == Stream.Null) response.Dispose();
-			}
+			if (response == null) return;
+			builder.StatusCode = (int)response.StatusCode;
+			builder.Stream = response.GetResponseStream();
+			// https://github.com/elastic/elasticsearch-net/issues/2311
+			// if stream is null call dispose on response instead.
+			if (builder.Stream == null || builder.Stream == Stream.Null) response.Dispose();
 		}
 
 		void IDisposable.Dispose() => this.DisposeManagedResources();