diff --git a/src/Mono.Android/Xamarin.Android.Net/AndroidClientHandler.cs b/src/Mono.Android/Xamarin.Android.Net/AndroidClientHandler.cs
index e1d6a138b10..6d8dfcdb551 100644
--- a/src/Mono.Android/Xamarin.Android.Net/AndroidClientHandler.cs
+++ b/src/Mono.Android/Xamarin.Android.Net/AndroidClientHandler.cs
@@ -91,7 +91,7 @@ public class AndroidClientHandler : HttpClientHandler
 		bool decompress_here;
 
 		URL java_url;
-		URLConnection java_connection;
+		HttpURLConnection java_connection;
 
 		/// <summary>
 		/// <para>
@@ -189,33 +189,30 @@ protected void AssertSelf ()
 			if (!request.RequestUri.IsAbsoluteUri)
 				throw new ArgumentException ("Must represent an absolute URI", "request");
 
-			/*using (*/java_url = new URL (request.RequestUri.ToString ());/*) {*/
-				/*using (*/java_connection = java_url.OpenConnection ();/*) {*/
-					HttpURLConnection httpConnection = SetupRequestInternal (request, java_connection);
+			java_url = new URL (request.RequestUri.ToString ());
+			java_connection = java_url.OpenConnection () as HttpURLConnection;
+			HttpURLConnection httpConnection = await SetupRequestInternal (request, java_connection).ConfigureAwait (false);
 					return await ProcessRequest (request, httpConnection, cancellationToken);
-				/*}
-			}*/
 		}
 		
-		async Task <HttpResponseMessage> ProcessRequest (HttpRequestMessage request, HttpURLConnection httpConnection, CancellationToken cancellationToken)
+		Task <HttpResponseMessage> ProcessRequest (HttpRequestMessage request, HttpURLConnection httpConnection, CancellationToken cancellationToken)
 		{
 			cancellationToken.ThrowIfCancellationRequested ();
 			httpConnection.InstanceFollowRedirects = AllowAutoRedirect;
 			RequestedAuthentication = null;
 			ProxyAuthenticationRequested = false;
 			
-			return await Task<HttpResponseMessage>.Factory.StartNew (() => DoProcessRequest (request, httpConnection, cancellationToken), cancellationToken).ConfigureAwait (false);
+			return DoProcessRequest (request, httpConnection, cancellationToken);
 		}
 		
-		HttpResponseMessage DoProcessRequest (HttpRequestMessage request, HttpURLConnection httpConnection, CancellationToken cancellationToken)
+		async Task <HttpResponseMessage> DoProcessRequest (HttpRequestMessage request, HttpURLConnection httpConnection, CancellationToken cancellationToken)
 		{
 			if (Logger.LogNet)
 				Logger.Log (LogLevel.Info, LOG_APP, $"{this}.DoProcessRequest ()");
-			httpConnection.RequestMethod = request.Method.ToString ();
 			try {
 				if (Logger.LogNet)
 					Logger.Log (LogLevel.Info, LOG_APP, $"  connecting");
-				httpConnection.Connect ();
+				await httpConnection.ConnectAsync ().ConfigureAwait (false);
 				if (Logger.LogNet)
 					Logger.Log (LogLevel.Info, LOG_APP, $"  connected");
 			} catch (Java.Net.ConnectException ex) {
@@ -372,9 +369,9 @@ void CopyHeaders (HttpURLConnection httpConnection, HttpResponseMessage response
 		/// </summary>
 		/// <param name="request">Request data</param>
 		/// <param name="conn">Pre-configured connection instance</param>
-		protected virtual void SetupRequest (HttpRequestMessage request, HttpURLConnection conn)
+		protected virtual Task SetupRequest (HttpRequestMessage request, HttpURLConnection conn)
 		{
-			AssertSelf ();
+			return Task.Factory.StartNew (AssertSelf);
 		}
 
 		/// <summary>
@@ -433,20 +430,20 @@ void AppendEncoding (string encoding, ref List <string> list)
 			list.Add (encoding);
 		}
 		
-		HttpURLConnection SetupRequestInternal (HttpRequestMessage request, URLConnection conn)
+		async Task <HttpURLConnection> SetupRequestInternal (HttpRequestMessage request, HttpURLConnection conn)
 		{
 			if (conn == null)
 				throw new ArgumentNullException (nameof (conn));
-			var httpConnection = conn.JavaCast <HttpURLConnection> ();
+			var httpConnection = conn;
 			if (httpConnection == null)
 				throw new InvalidOperationException ($"Unsupported URL scheme {conn.URL.Protocol}");
-
+			httpConnection.RequestMethod = request.Method.ToString ();
 			// SSL context must be set up as soon as possible, before adding any content or
 			// headers. Otherwise Java won't use the socket factory
-			SetupSSL (httpConnection as HttpsURLConnection);
+			await SetupSSL (httpConnection as HttpsURLConnection);
 			if (request.Content != null)
-				AddHeaders (httpConnection, request.Content.Headers);
-			AddHeaders (httpConnection, request.Headers);
+				await AddHeaders (httpConnection, request.Content.Headers);
+			await AddHeaders (httpConnection, request.Headers);
 			
 			List <string> accept_encoding = null;
 
@@ -475,15 +472,16 @@ HttpURLConnection SetupRequestInternal (HttpRequestMessage request, URLConnectio
 					httpConnection.SetRequestProperty ("Cookie", cookieHeaderValue);
 			}
 			
-			HandlePreAuthentication (httpConnection);
-			SetupRequest (request, httpConnection);
-			SetupRequestBody (httpConnection, request);
+			await HandlePreAuthentication (httpConnection);
+			await SetupRequest (request, httpConnection);
+			await SetupRequestBody (httpConnection, request);
 			
 			return httpConnection;
 		}
 
-		void SetupSSL (HttpsURLConnection httpsConnection)
+		Task SetupSSL (HttpsURLConnection httpsConnection)
 		{
+			return Task.Factory.StartNew (() => {
 			if (httpsConnection == null)
 				return;
 
@@ -516,10 +514,12 @@ void SetupSSL (HttpsURLConnection httpsConnection)
 			SSLContext context = SSLContext.GetInstance ("TLS");
 			context.Init (kmf?.GetKeyManagers (), tmf.GetTrustManagers (), null);
 			httpsConnection.SSLSocketFactory = context.SocketFactory;
+			});
 		}
 		
-		void HandlePreAuthentication (HttpURLConnection httpConnection)
+		Task HandlePreAuthentication (HttpURLConnection httpConnection)
 		{
+			return Task.Factory.StartNew (() => {
 			AuthenticationData data = PreAuthenticationData;
 			if (!PreAuthenticate || data == null)
 				return;
@@ -548,37 +548,55 @@ void HandlePreAuthentication (HttpURLConnection httpConnection)
 			if (Logger.LogNet)
 				Logger.Log (LogLevel.Info, LOG_APP, $"Authentication header '{data.UseProxyAuthentication ? "Proxy-Authorization" : "Authorization"}' will be set to '{authorization.Message}'");
 			httpConnection.SetRequestProperty (data.UseProxyAuthentication ? "Proxy-Authorization" : "Authorization", authorization.Message);
+			});
 		}
 
-		void AddHeaders (HttpURLConnection conn, HttpHeaders headers)
+		Task AddHeaders (HttpURLConnection conn, HttpHeaders headers)
 		{
+			return Task.Factory.StartNew (() => {
 			if (headers == null)
 				return;
 
 			foreach (KeyValuePair<string, IEnumerable<string>> header in headers) {
 				conn.SetRequestProperty (header.Key, header.Value != null ? String.Join (",", header.Value) : String.Empty);
 			}
+			});
 		}
 		
-		void SetupRequestBody (HttpURLConnection conn, HttpRequestMessage request)
+		async Task SetupRequestBody (HttpURLConnection httpConnection, HttpRequestMessage request)
 		{
 			if (request.Content == null) {
+				httpConnection.SetChunkedStreamingMode (0);
 				// Pilfered from System.Net.Http.HttpClientHandler:SendAync
 				if (HttpMethod.Post.Equals (request.Method) || HttpMethod.Put.Equals (request.Method) || HttpMethod.Delete.Equals (request.Method)) {
 					// Explicitly set this to make sure we're sending a "Content-Length: 0" header.
 					// This fixes the issue that's been reported on the forums:
 					// http://forums.xamarin.com/discussion/17770/length-required-error-in-http-post-since-latest-release
-					conn.SetRequestProperty ("Content-Length", "0");
+					httpConnection.SetRequestProperty ("Content-Length", "0");
 				}
 				return;
 			}
 			
-			conn.DoOutput = true;
-			long? contentLength = request.Content.Headers.ContentLength;
-			if (contentLength != null)
-				conn.SetFixedLengthStreamingMode ((int)contentLength);
+			httpConnection.DoOutput = true;
+
+			var bytes = await request.Content.ReadAsByteArrayAsync ().ConfigureAwait (false);
+
+			int contentLength = bytes.Length;
+			httpConnection.SetRequestProperty ("Content-Length", contentLength.ToString());
+			httpConnection.SetFixedLengthStreamingMode (contentLength);
+
+			string contentType;
+			if (request.Content.Headers.ContentType != null)
+				contentType = String.Join (" ", request.Content.Headers.GetValues ("Content-Type"));
 			else
-				conn.SetChunkedStreamingMode (0);
+				contentType = "text/plain";
+			httpConnection.SetRequestProperty ("Content-Type", contentType);
+
+			await Task.Factory.StartNew (() => {
+				httpConnection.OutputStream.Write (bytes, 0, contentLength);
+				httpConnection.OutputStream.Flush ();
+				httpConnection.OutputStream.Close ();
+			});
 		}
 	}
 }